Pimavanserin supplier | CasNO.706779-91-1

Name
Pimavanserin
EINECS 1806241-263-5
CAS No. 706779-91-1
Article Data39
CAS DataBase
Density 1.15 g/cm³
Solubility
Melting Point 100-103 oC
Formula C₂₅H₃₄FN₃O₂
Boiling Point 604.222 °C at 760 mmHg
Molecular Weight 427.562
Flash Point 319.222 °C
Transport Information
Appearance Pale Yellow to Pale Orange Solid
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms N-(4-Fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-[[4-(2-methylpropyloxy)phenyl]methyl]carbamide;1-(4-Fluorobenzyl)-3-(4-isobutoxybenzyl)-1-(1-methylpiperidin-4-yl)urea;
PSA 44.81000
LogP 4.99530

Synthetic route

: 1-[4-(2-methylpropyloxy)phenyl]methanamino acetate

: C18H24FN4O(1+)*I(1-)

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
In toluene at 50℃; for 15h;	100%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: 530-62-1
1,1'-carbonyldiimidazole

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 1-[4-(2-methylpropyloxy)phenyl]methanamine; 1,1'-carbonyldiimidazole In toluene at 20℃; for 1h; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In toluene at 50℃; for 15h;	96%
Stage #1: 1-[4-(2-methylpropyloxy)phenyl]methanamine; 1,1'-carbonyldiimidazole In dichloromethane at 0 - 5℃; for 0.5h; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In dichloromethane at 18 - 22℃; for 12h; Temperature;	85%

...Expand

: N-(4-(2-methylpropyloxy)phenylmethyl)imidazol-1-ylcarboxamide

: N-(4-fluorobenzyl)-1-methylpiperidine-4-amine dihydrochloride

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With potassium carbonate at 65 - 70℃; for 18h;	95.6%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 74124-79-1
di(succinimido) carbonate

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine; di(succinimido) carbonate With 4-methyl-morpholine In dichloromethane at -5 - 25℃; for 5h; Stage #2: 1-[4-(2-methylpropyloxy)phenyl]methanamine In dichloromethane at 25℃; for 10h; Solvent; Temperature; Time;	95%

...Expand

: 1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-(1-methylpiperidin-4-yl)thiourea

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With silver carbonate In acetonitrile at 20℃; for 24h; Reagent/catalyst; Green chemistry;	94.2%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: N-(4-isobutoxybenzyl)carbamic acid phenyl ester

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With potassium carbonate In toluene at 90℃; for 24h; Reagent/catalyst; Temperature;	92%
With triethylamine In ethanol for 6h; Reflux;	91%
With triethylamine In ethanol for 12h; Reflux; Green chemistry;	84.5%

: 1-(4-fluorobenzyl)-1-(1-methylpiperidin-4-yl)urea

: 18962-07-7
4-isobutoxybenzaldehyde

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 1-(4-fluorobenzyl)-1-(1-methylpiperidin-4-yl)urea; 4-isobutoxybenzaldehyde With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 10h; Stage #2: With sodium tetrahydroborate at -5 - 0℃; for 6h;	92%
With 1,1,3,3-Tetramethyldisiloxane; trifluoroacetic acid In toluene for 24h; Reagent/catalyst; Solvent; Time; Inert atmosphere;	82%

: 4-isobutoxybenzylamine acetate

: N-(4-fluorobenzyl)-1-methylpiperidin-4-amine oxalate

: 530-62-1
1,1'-carbonyldiimidazole

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 4-isobutoxybenzylamine acetate; 1,1'-carbonyldiimidazole With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 5℃; for 0.5h; Stage #2: N-(4-fluorobenzyl)-1-methylpiperidin-4-amine oxalate With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃; for 10h;	90.4%

...Expand

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 4-isobutoxybenzylamine acetate

: 530-62-1
1,1'-carbonyldiimidazole

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 4-isobutoxybenzylamine acetate; 1,1'-carbonyldiimidazole With triethylamine In dichloromethane at 0 - 5℃; for 0.5h; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In dichloromethane at 15 - 25℃; for 8h;	90.3%

...Expand

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: phenyl (4-fluorobenzyl)(1-methylpiperidin-4-yl)carbamate

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With N,N'-bis(4-isobutoxybenzyl)urea; potassium carbonate In toluene at 65 - 80℃; for 5h; Reagent/catalyst; Temperature;	90%
With triethylamine In acetonitrile at 50 - 60℃; for 12h;	75%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 61904-59-4
(4-Isobutoxy-phenyl)-acetic acid hydrazide

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium nitrite In dichloromethane; water at 15 - 110℃; under 11251.1 Torr; for 0.0611111h; Time; Solvent; Temperature;	90%

: 590-28-3
potassium cyanate

: N-(4-fluorobenzyl)-1-methylpiperidine-4-amine dihydrochloride

: 18962-07-7
4-isobutoxybenzaldehyde

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: potassium cyanate; N-(4-fluorobenzyl)-1-methylpiperidine-4-amine dihydrochloride In methanol for 4h; Stage #2: 4-isobutoxybenzaldehyde With 1,1,3,3-Tetramethyldisiloxane; trifluoroacetic acid for 4h; Reflux;	88%

...Expand

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: N-(4-(2-methylpropyloxy)phenylmethyl)imidazol-1-ylcarboxamide

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
In toluene at 25 - 55℃; for 15h;	83.19%
In tetrahydrofuran at 60℃; for 4h;	70%
In toluene Solvent; Reflux;
In N,N-dimethyl-formamide; acetonitrile at 60℃; for 2h; Temperature; Solvent; Sealed tube;	704.3 mg
With potassium tert-butylate In toluene at 25 - 55℃; for 15h; Reflux;	16 g

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 1-(4-isobutoxybenzyl)urea

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
at 120 - 130℃; for 12h; Green chemistry;	83.1%
In toluene

: 1-[4-(2-methylpropyloxy)phenyl]methanamino acetate

: C18H24FN4O(1+)*I(1-)

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
In toluene at 50℃; for 15h;	100%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: 530-62-1
1,1'-carbonyldiimidazole

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 1-[4-(2-methylpropyloxy)phenyl]methanamine; 1,1'-carbonyldiimidazole In toluene at 20℃; for 1h; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In toluene at 50℃; for 15h;	96%
Stage #1: 1-[4-(2-methylpropyloxy)phenyl]methanamine; 1,1'-carbonyldiimidazole In dichloromethane at 0 - 5℃; for 0.5h; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In dichloromethane at 18 - 22℃; for 12h; Temperature;	85%

...Expand

: N-(4-(2-methylpropyloxy)phenylmethyl)imidazol-1-ylcarboxamide

: N-(4-fluorobenzyl)-1-methylpiperidine-4-amine dihydrochloride

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With potassium carbonate at 65 - 70℃; for 18h;	95.6%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 74124-79-1
di(succinimido) carbonate

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine; di(succinimido) carbonate With 4-methyl-morpholine In dichloromethane at -5 - 25℃; for 5h; Stage #2: 1-[4-(2-methylpropyloxy)phenyl]methanamine In dichloromethane at 25℃; for 10h; Solvent; Temperature; Time;	95%

...Expand

: 1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-(1-methylpiperidin-4-yl)thiourea

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With silver carbonate In acetonitrile at 20℃; for 24h; Reagent/catalyst; Green chemistry;	94.2%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: N-(4-isobutoxybenzyl)carbamic acid phenyl ester

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With potassium carbonate In toluene at 90℃; for 24h; Reagent/catalyst; Temperature;	92%
With triethylamine In ethanol for 6h; Reflux;	91%
With triethylamine In ethanol for 12h; Reflux; Green chemistry;	84.5%

: 1-(4-fluorobenzyl)-1-(1-methylpiperidin-4-yl)urea

: 18962-07-7
4-isobutoxybenzaldehyde

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 1-(4-fluorobenzyl)-1-(1-methylpiperidin-4-yl)urea; 4-isobutoxybenzaldehyde With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 10h; Stage #2: With sodium tetrahydroborate at -5 - 0℃; for 6h;	92%
With 1,1,3,3-Tetramethyldisiloxane; trifluoroacetic acid In toluene for 24h; Reagent/catalyst; Solvent; Time; Inert atmosphere;	82%

: 4-isobutoxybenzylamine acetate

: N-(4-fluorobenzyl)-1-methylpiperidin-4-amine oxalate

: 530-62-1
1,1'-carbonyldiimidazole

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 4-isobutoxybenzylamine acetate; 1,1'-carbonyldiimidazole With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 5℃; for 0.5h; Stage #2: N-(4-fluorobenzyl)-1-methylpiperidin-4-amine oxalate With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃; for 10h;	90.4%

...Expand

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 4-isobutoxybenzylamine acetate

: 530-62-1
1,1'-carbonyldiimidazole

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 4-isobutoxybenzylamine acetate; 1,1'-carbonyldiimidazole With triethylamine In dichloromethane at 0 - 5℃; for 0.5h; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In dichloromethane at 15 - 25℃; for 8h;	90.3%

...Expand

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: phenyl (4-fluorobenzyl)(1-methylpiperidin-4-yl)carbamate

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With N,N'-bis(4-isobutoxybenzyl)urea; potassium carbonate In toluene at 65 - 80℃; for 5h; Reagent/catalyst; Temperature;	90%
With triethylamine In acetonitrile at 50 - 60℃; for 12h;	75%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 61904-59-4
(4-Isobutoxy-phenyl)-acetic acid hydrazide

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium nitrite In dichloromethane; water at 15 - 110℃; under 11251.1 Torr; for 0.0611111h; Time; Solvent; Temperature;	90%

: 590-28-3
potassium cyanate

: N-(4-fluorobenzyl)-1-methylpiperidine-4-amine dihydrochloride

: 18962-07-7
4-isobutoxybenzaldehyde

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: potassium cyanate; N-(4-fluorobenzyl)-1-methylpiperidine-4-amine dihydrochloride In methanol for 4h; Stage #2: 4-isobutoxybenzaldehyde With 1,1,3,3-Tetramethyldisiloxane; trifluoroacetic acid for 4h; Reflux;	88%

...Expand

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: N-(4-(2-methylpropyloxy)phenylmethyl)imidazol-1-ylcarboxamide

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
In toluene at 25 - 55℃; for 15h;	83.19%
In tetrahydrofuran at 60℃; for 4h;	70%
In toluene Solvent; Reflux;
In N,N-dimethyl-formamide; acetonitrile at 60℃; for 2h; Temperature; Solvent; Sealed tube;	704.3 mg
With potassium tert-butylate In toluene at 25 - 55℃; for 15h; Reflux;	16 g

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 1-(4-isobutoxybenzyl)urea

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
at 120 - 130℃; for 12h; Green chemistry;	83.1%
In toluene

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: 1885-14-9
phenyl chloroformate

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 1-[4-(2-methylpropyloxy)phenyl]methanamine; phenyl chloroformate With triethylamine In acetonitrile at 0 - 20℃; for 2h; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine With triethylamine In acetonitrile at 60℃; for 12h;	83%

...Expand

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 24424-99-5
di-tert-butyl dicarbonate

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: di-tert-butyl dicarbonate; 1-[4-(2-methylpropyloxy)phenyl]methanamine With dmap; triethylamine In dichloromethane at -18 - -5℃; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In dichloromethane at -5 - 35℃; for 0.5h;	83%
Stage #1: di-tert-butyl dicarbonate; 1-[4-(2-methylpropyloxy)phenyl]methanamine With dmap In acetonitrile at -10℃; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In toluene at 50℃; for 15h;

...Expand

: 32315-10-9
bis(trichloromethyl) carbonate

: N-(4-fluorobenzyl)-1-methylpiperidin-4-amine p-toluenesulfonate

: 4-isobutoxybenzylamine hydrochloride

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; 4-isobutoxybenzylamine hydrochloride With N-ethyl-N,N-diisopropylamine In chloroform at -5 - 5℃; for 1h; Stage #2: N-(4-fluorobenzyl)-1-methylpiperidin-4-amine p-toluenesulfonate With N-ethyl-N,N-diisopropylamine In chloroform at 15 - 25℃; for 6h;	82.4%

...Expand

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: C16H20N2O5

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With potassium carbonate In Isopropyl acetate at 50 - 60℃; for 6h; Solvent; Temperature;	82%
at 80℃; for 3h;	20.3 g

: 639863-75-5
1-(isocyanatomethyl)-4-(2-methylpropoxy)benzene

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h; Large scale;	81.6%
In tetrahydrofuran at 25℃; for 16h; Solvent;	63.8%
In tetrahydrofuran at 20℃; for 16h;	60.4%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 32315-10-9
bis(trichloromethyl) carbonate

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; 1-[4-(2-methylpropyloxy)phenyl]methanamine With triethylamine In dichloromethane at -5 - 5℃; for 1h; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In dichloromethane at 15 - 25℃; for 5h; Temperature; Solvent;	81.6%

...Expand

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 4-nitrophenyl (4-isobutoxybenzyl)carbamate

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃; for 2h;	81%

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: (4-fluorobenzyl)(1-methylpiperidin-4-yl)carbamoyl chloride

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With dmap In 1,4-dioxane at 75℃; for 15h; Solvent; Reagent/catalyst; Temperature;	78.5%

: 4-isobutoxybenzylamine acetate

: N-(4-fluorobenzyl)-1-methylpiperidin-4-amine oxalate

: 7693-46-1
4-Nitrophenyl chloroformate

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 4-isobutoxybenzylamine acetate; 4-Nitrophenyl chloroformate With triethylamine In dichloromethane at 0 - 5℃; for 0.5h; Stage #2: N-(4-fluorobenzyl)-1-methylpiperidin-4-amine oxalate With triethylamine In dichloromethane at 15 - 25℃; for 10h;	78.1%

...Expand

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: N-(4-isobutoxybenzyl)formamide

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: N-(4-isobutoxybenzyl)formamide With bis(trichloromethyl) carbonate; triethylamine In dichloromethane at 0 - 20℃; Green chemistry; Stage #2: With trifluoromethylsulfonic anhydride; dimethyl sulfoxide at -65 - -60℃; Inert atmosphere; Green chemistry; Stage #3: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In dichloromethane at -65 - 20℃; Inert atmosphere; Green chemistry;	77.7%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: 7693-46-1
4-Nitrophenyl chloroformate

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 1-[4-(2-methylpropyloxy)phenyl]methanamine; 4-Nitrophenyl chloroformate With triethylamine In acetonitrile at 0 - 20℃; for 2h; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine With triethylamine In acetonitrile at 0 - 20℃; for 12h; Cooling with ice;	74%

...Expand

: 1-(4-fluorobenzyl)-1-(1-methylpiperidin-4-yl)urea

: sodium hydroxy(4-isobutoxyphenyl)methanesulfonate

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With triethylsilane; trifluoroacetic acid In acetonitrile at 50℃; for 24h; Inert atmosphere;	74%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: 1-[4-(2-methylpropyloxy)phenyl]methanamine With dmap; di-tert-butyl dicarbonate; triethylamine In dichloromethane at -5 - 5℃; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In dichloromethane at 0 - 5℃; for 2h; Reagent/catalyst; Further stages;	72%

: 4734-09-2
1-[4-(2-methylpropyloxy)phenyl]methanamine

: 4-((-4-fluorobenzyl)benzyloxycarbonylamino)-1-methylpiperidine

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 40℃; for 10h;	71.8%

: 359878-47-0
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

: methyl (4-isobutoxybenzyl)carbamate

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

Conditions

Conditions	Yield
Stage #1: methyl (4-isobutoxybenzyl)carbamate With triethylamine In toluene at 0 - 10℃; for 0.5h; Stage #2: N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine In toluene at 80℃; for 12h;	71%
at 120℃; for 0.24h; Time; Temperature;	22%
With potassium tert-butylate In toluene for 5h; Reflux;	14 g

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

: 87-69-4
L-Tartaric acid

: 1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-(1-methylpiperidin-4-yl)urea L-hemitartrate

Conditions

Conditions	Yield
In n-heptane; acetone at 20 - 50℃; for 10h; Solvent;	99%
In ethanol at -5 - 50℃; for 16h;	85%
In ethanol at 20 - 50℃; for 17h;	104.6 g
In ethanol at 20 - 50℃; for 2h;	21.9 g

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

: 104-15-4
toluene-4-sulfonic acid

: C25H34FN3O2*C7H8O3S*H2O

Conditions

Conditions	Yield
In ethyl acetate at 20 - 42℃; for 5h;	97.9%

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

: 87-69-4
L-Tartaric acid

: Pimavanserin tartrate

Conditions

Conditions	Yield
In tert-butyl methyl ether; acetone at 50 - 55℃; for 1h;	95%
In dichloromethane; isopropyl alcohol at 70℃; for 5h; Inert atmosphere;	93%
In dichloromethane; isopropyl alcohol at 0 - 70℃; for 7h; Inert atmosphere;	93%

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

: 100-88-9
cyclohexylsulfamic acid

: C25H34FN3O2*H2O*C6H13NO3S

Conditions

Conditions	Yield
In ethyl acetate at 20 - 42℃; for 5h;	93.7%

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

: 87-69-4
L-Tartaric acid

: pimavanserin tartrate

Conditions

Conditions	Yield
In ethanol at 30 - 50℃; for 2h;	85%

: 706779-91-1
N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide

: 147-71-7
D-tartaric acid

: N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropoxy)phenylmethyl)urea hemi-tartrate

Conditions

Conditions	Yield
In ethanol	85%

Pimavanserin History

As of April 2009, pimavanserin is in Phase III clinical trials for the treatment of Parkinson's disease psychosis, and is in Phase II trials for adjunctive treatment of schizophrenia alongside an antipsychotic medication.

Pimavanserin Specification

The Pimavanserin, with the CAS registry number 706779-91-1, is also known as N-(4-Fluorophenylmethyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)phenylmethyl)carbamide. It belongs to the product categories of Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C₂₅H₃₄FN₃O₂ and molecular weight is 427.55. What's more, both its IUPAC name and systematic name are the same which is called 1-[(4-Fluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[[4-(2-methylpropoxy)phenyl]methyl]urea. Pimavanserin is a drug developed by Acadia Pharmaceuticals which acts as an inverse agonist on the serotonin receptor subtype 5-HT_2A, with 10x selectivity over 5-HT_2C, and no significant affinity or activity at 5-HT_2B or dopamine receptors. When you are dealing with this chemical, you should be very careful. This chemical may cause inflammation to the skin or other mucous membranes.

Physical properties about Pimavanserin are: (1)ACD/LogP: 4.09; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 3; (5)ACD/BCF (pH 5.5): 2; (6)ACD/BCF (pH 7.4): 44; (7)ACD/KOC (pH 5.5): 9 ; (8)ACD/KOC (pH 7.4): 173; (9)#H bond acceptors: 5 ; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 44.81 Å²; (13)Index of Refraction: 1.576; (14)Molar Refractivity: 122.952 cm³; (15)Molar Volume: 371.779 cm³; (16)Surface Tension: 47.65 dyne/cm; (17)Density: 1.15 g/cm³; (18)Flash Point: 319.222 °C; (19)Enthalpy of Vaporization: 89.857 kJ/mol; (20)Boiling Point: 604.222 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: Fc1ccc(cc1)CN(C(=O)NCc2ccc(OCC(C)C)cc2)C3CCN(C)CC3
(2) InChI: InChI=1S/C25H34FN3O2/c1-19(2)18-31-24-10-6-20(7-11-24)16-27-25(30)29(23-12-14-28(3)15-13-23)17-21-4-8-22(26)9-5-21/h4-11,19,23H,12-18H2,1-3H3,(H,27,30)
(3) InChIKey: RKEWSXXUOLRFBX-UHFFFAOYSA-N

Product Name

Pimavanserin

Synthetic route

Pimavanserin History

Pimavanserin Specification

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