N-Benzylpiperidine-4-carboxaldehyde supplier

Name
N-Benzylpiperidine-4-carboxaldehyde
EINECS 244-757-7
CAS No. 22065-85-6
Article Data32
CAS DataBase
Density 1.114 g/cm³
Solubility
Melting Point 315
Formula C₁₃H₁₇NO
Boiling Point 299.5 °C at 760 mmHg
Molecular Weight 203.284
Flash Point 104.3 °C
Transport Information UN 2810 6.1/PG 3
Appearance colorless oil
Safety 26-28-36/37/39
Risk Codes 25-41
Molecular Structure
Hazard Symbols T
Synonyms Isonipecotaldehyde,1-benzyl- (8CI);1-Benzyl-4-formylpiperidine;1-Benzyl-4-piperidinecarboxaldehyde;4-Formyl-1-(phenylmethyl)piperidine;4-Formyl-1-benzylpiperidine;N-(Phenylmethyl)piperidine-4-carboxaldehyde;N-Benzyl-4-formylpiperidine;N-Benzyl-4-piperidinecarbaldehyde;
PSA 20.31000
LogP 2.03540

Synthetic route

: 62718-31-4
1-benzylpiperidine-4-carbonitrile

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Stage #1: 1-benzylpiperidine-4-carbonitrile With diisobutylaluminium hydride In toluene at 0℃; for 1h; Stage #2: With water; sodium hydroxide In methanol; toluene for 0.5h; pH=8; Temperature;	97.5%

: 10315-06-7
1-benzyl-4-piperidinecarboxylic acid methyl ester

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
With red-aluminum/morpholine complex In toluene at -5 - 0℃; for 0.5h; Reagent/catalyst; Solvent; Inert atmosphere; Large scale;	96.5%
Multi-step reaction with 2 steps 1: 69.5 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 50 °C 2: 94.3 percent / oxalyl chloride; dimethyl sulfoxide; Et3N / CH2Cl2 / 0.25 h / -55 °C View Scheme
Multi-step reaction with 4 steps 1.1: water; methanol; sodium hydroxide / 2 h / Reflux 2.1: thionyl chloride / 2 h / Reflux 2.2: 0.5 h / Cooling with ice 3.1: thionyl chloride / 5 h / Reflux 4.1: diisobutylaluminium hydride / toluene / 1 h / 0 °C 4.2: 0.5 h / pH 8 View Scheme

: 67686-01-5
1-benzyl-4-piperidinemethanol

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -70 - 20℃; Swern Oxidation;	96%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -55℃; for 0.25h; Swern oxidation;	94.3%
Stage #1: 1-benzyl-4-piperidinemethanol With dimethylsulfide; triethylamine In toluene at -15 - -10℃; Inert atmosphere; Stage #2: With N-chloro-succinimide In toluene	85%

: 24228-40-8
N-benzyl isonipecotic acid ethyl ester

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
With diisobutylaluminium hydride In hexane; toluene at -78℃; for 2.5h; Flow reactor;	96%
With Red-ALP-KTB In various solvent(s) at 10℃;	95%
Stage #1: N-benzyl isonipecotic acid ethyl ester With morpholine; diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 3.16667h; Inert atmosphere; Stage #2: With lithium diisobutylmethoxy aluminum hydride In tetrahydrofuran; hexane at 0℃; for 0.166667h; Inert atmosphere;	94%

: 123-75-1
pyrrolidine

: 24228-40-8
N-benzyl isonipecotic acid ethyl ester

A: 22065-85-6
1-benzyl-4-formylpiperidine

B: 67686-01-5
1-benzyl-4-piperidinemethanol

C: N-benzyl-4-(pyrrolidin-1-ylmethyl)piperidine

D: N-benzyl-4-(pyrrolidin-1-ylcarbonyl)piperidine

Conditions

Conditions	Yield
With Red-ALP In various solvent(s) at 20℃; for 2h;	A 95% B n/a C n/a D n/a

...Expand

: 503544-95-4
1-benzyl-1,2,3,6-tetrahydropyridine-4-carbaldehyde

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 3h;	90%

: 1-benzyl-N,N-dimethylpiperidine-4-carboxamide

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
With sodium hydride; sodium iodide In tetrahydrofuran at 60℃; chemoselective reaction;	75%

: 42790-44-3
1-benzyl-4-vinyl-piperidine

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
With PYRIMIDINE; sodium periodate; osmium(VIII) oxide In 1,4-dioxane; 2-methyl-propan-1-ol; water at 20℃; for 7h;	74%

: C14H16NO3(1-)*Na(1+)

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Stage #1: C14H16NO3(1-)*Na(1+) With hydrogenchloride; water at 90℃; for 1.5 - 2h; Heating / reflux; Stage #2: With ammonia In water at 15℃; pH=8.5 - 9.0; Product distribution / selectivity;	68%

: 3612-20-2
1-phenylmethyl-4-piperidone

: 18107-18-1
diazomethyl-trimethyl-silane

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Stage #1: diazomethyl-trimethyl-silane With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 1.25h; Stage #2: 1-phenylmethyl-4-piperidone In tetrahydrofuran at -78 - 20℃; for 4h; Heating / reflux;	55%
With N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide

: 101775-64-8
1-benzyl-4-methoxymethyl-piperidine

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Stage #1: 1-benzyl-4-methoxymethyl-piperidine With hydrogenchloride; methanol; water for 3h; Heating / reflux; Stage #2: With sodium hydroxide In water pH=12;	54%

: 120014-33-7
1-Benzyl-4-(methoxymethylidene)-piperidine

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Stage #1: 1-Benzyl-4-(methoxymethylidene)-piperidine With hydrogenchloride In methanol; water for 3h; Heating / reflux; Stage #2: With sodium hydroxide In water pH=12;	54%
With hydrogenchloride; potassium carbonate In tetrahydrofuran
With formic acid In water at 35℃; for 3h; Inert atmosphere; Large scale;	57.7 kg

: 19867-34-6
N-benzyl-1-oxa-6-azaspiro[2,5]-octane

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
With magnesium bromide ethyl etherate In benzene at 40℃; for 0.333333h;	17.5 g

: 3612-20-2
1-phenylmethyl-4-piperidone

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrabutylammonium bromide; NaOH / toluene; H2O / 4 h / 80 °C 2: 17.5 g / magnesium bromide etherate / benzene / 0.33 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium t-butanolate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere; Large scale 1.2: 1 h / 5 °C / Large scale 2.1: formic acid / water / 3 h / 35 °C / Inert atmosphere; Large scale View Scheme

: 330173-08-5
N-benzyl-2-(4-methylphenylsulfonyl)acetamide

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 0.25 h / 20 °C 1.2: 95 percent / tetrahydrofuran / 5 h / Heating 2.1: 90 percent / AlCl3; LiAlH4 / tetrahydrofuran / 3 h / 20 °C 3.1: 90 percent / HCl / acetone; H2O / 24 h / Heating 4.1: 90 percent / H2 / Pd/C / methanol / 3 h / 20 °C View Scheme

: 1-benzyl-3-(4-methylphenylsulfonyl)-4-dimethoxymethylpiperidine-2,6-dione

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / AlCl3; LiAlH4 / tetrahydrofuran / 3 h / 20 °C 2: 90 percent / HCl / acetone; H2O / 24 h / Heating 3: 90 percent / H2 / Pd/C / methanol / 3 h / 20 °C View Scheme

: 1-benzyl-4-(dimethoxymethyl)-3-(p-tolylsulfonyl)piperidine

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / HCl / acetone; H2O / 24 h / Heating 2: 90 percent / H2 / Pd/C / methanol / 3 h / 20 °C View Scheme

: 1126-09-6
4-carbethoxypiperidine

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / NaHCO3 / ethanol; H2O / 2 h / 80 °C 2: 95 percent / Red-ALP-KTB / various solvent(s) / 10 °C View Scheme
Multi-step reaction with 3 steps 1: 76 percent / K2CO3 / ethanol / 72 h / Ambient temperature 2: 61 percent / LiAlH4 / tetrahydrofuran / 18 h / Heating 3: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, from -65 deg C to -60 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT, 6 h View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / toluene / 10 - 75 °C / Large scale 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 15 - 30 °C / Large scale 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -65 - -45 °C / Large scale 3.2: 0.5 h / -50 - -45 °C / Large scale View Scheme

: 100-44-7
benzyl chloride

Fmoc-(S)-leucine bound to Wang resin: Fmoc-(S)-leucine bound to Wang resin

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / NaHCO3 / ethanol; H2O / 2 h / 80 °C 2: 95 percent / Red-ALP-KTB / various solvent(s) / 10 °C View Scheme

: 498-94-2
isonipecotic acid

paraformaldehyde: paraformaldehyde

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 84 percent / SOCl2 / 20 h / 20 °C 2: 79.7 percent / Et3N / CH2Cl2 / 20 °C 3: 69.5 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 50 °C 4: 94.3 percent / oxalyl chloride; dimethyl sulfoxide; Et3N / CH2Cl2 / 0.25 h / -55 °C View Scheme

: 7462-86-4
methyl piperidine-4-carboxylate hydrochloride

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 79.7 percent / Et3N / CH2Cl2 / 20 °C 2: 69.5 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 50 °C 3: 94.3 percent / oxalyl chloride; dimethyl sulfoxide; Et3N / CH2Cl2 / 0.25 h / -55 °C View Scheme
Multi-step reaction with 5 steps 1.1: triethylamine / methanol / 6 h / Reflux 2.1: water; methanol; sodium hydroxide / 2 h / Reflux 3.1: thionyl chloride / 2 h / Reflux 3.2: 0.5 h / Cooling with ice 4.1: thionyl chloride / 5 h / Reflux 5.1: diisobutylaluminium hydride / toluene / 1 h / 0 °C 5.2: 0.5 h / pH 8 View Scheme

: 100-39-0
benzyl bromide

t-BuOCOCH2-X: t-BuOCOCH2-X

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 79.7 percent / Et3N / CH2Cl2 / 20 °C 2: 69.5 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 50 °C 3: 94.3 percent / oxalyl chloride; dimethyl sulfoxide; Et3N / CH2Cl2 / 0.25 h / -55 °C View Scheme

: 100-44-7
benzyl chloride

metal: metal

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent / K2CO3 / ethanol / 72 h / Ambient temperature 2: 61 percent / LiAlH4 / tetrahydrofuran / 18 h / Heating 3: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, from -65 deg C to -60 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT, 6 h View Scheme

: 3612-20-2
1-phenylmethyl-4-piperidone

: 4009-98-7
(methoxymethyl)triphenylphosphonium chloride

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Stage #1: (methoxymethyl)triphenylphosphonium chloride With n-butyllithium In diethyl ether; hexane at 0 - 20℃; for 0.5h; Stage #2: 1-phenylmethyl-4-piperidone In diethyl ether; hexane at 20℃; for 3h; Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages;

: 100-44-7
benzyl chloride

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / toluene / 10 - 75 °C / Large scale 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 15 - 30 °C / Large scale 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -65 - -45 °C / Large scale 3.2: 0.5 h / -50 - -45 °C / Large scale View Scheme
Multi-step reaction with 3 steps 1.1: toluene / 2 h / 10 - 15 °C 1.2: 6 h / 70 °C 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 15 - 30 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -55 - -48 °C 3.2: 1.08 h / -55 - -20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / ethanol / 3 h / Reflux; Large scale 2: red-aluminum/morpholine complex / toluene / 0.5 h / -5 - 0 °C / Inert atmosphere; Large scale View Scheme
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / ethanol / 3 h / Reflux 2: red-aluminum/morpholine complex / cyclohexane / 3 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / toluene / 0.25 h 1.2: 4 h / 100 °C 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C / Inert atmosphere 3.1: dimethyl sulfoxide; oxalyl dichloride; triethylamine / dichloromethane / -70 - 20 °C View Scheme

: 4-piperidinecarboxylic acid methyl ester hydrochloride

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / ethanol / 3 h / Reflux; Large scale 2: red-aluminum/morpholine complex / toluene / 0.5 h / -5 - 0 °C / Inert atmosphere; Large scale View Scheme

: 100-52-7
benzaldehyde

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; platinum on activated charcoal / toluene / 80 °C / Flow reactor 2: diisobutylaluminium hydride / toluene; hexane / 2.5 h / -78 °C / Flow reactor View Scheme

: 62992-68-1
1-benzyl-piperidine-4-carboxylic acid amide

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: thionyl chloride / 5 h / Reflux 2.1: diisobutylaluminium hydride / toluene / 1 h / 0 °C 2.2: 0.5 h / pH 8 View Scheme

: 498-94-2
isonipecotic acid

: 22065-85-6
1-benzyl-4-formylpiperidine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: thionyl chloride / 2 h / Reflux 2.1: triethylamine / methanol / 6 h / Reflux 3.1: water; methanol; sodium hydroxide / 2 h / Reflux 4.1: thionyl chloride / 2 h / Reflux 4.2: 0.5 h / Cooling with ice 5.1: thionyl chloride / 5 h / Reflux 6.1: diisobutylaluminium hydride / toluene / 1 h / 0 °C 6.2: 0.5 h / pH 8 View Scheme

: 2107-69-9
5,6-dimethoxy-1-indanone

: 22065-85-6
1-benzyl-4-formylpiperidine

: 120014-07-5
1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine

Conditions

Conditions	Yield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water; toluene at 20℃; Product distribution / selectivity; Inert atmosphere; Reflux;	100%
With sodium methylate In methanol; ethanol at 79℃; for 1.58333h; Product distribution / selectivity; Heating / reflux;	93.4%
With sodium methylate In methanol at 66℃; for 1h; Product distribution / selectivity; Heating / reflux;	93.9%

: 22065-85-6
1-benzyl-4-formylpiperidine

: 89343-06-6
tris-iso-propylsilyl acetylene

: (R)-(-)-1-(N-benzyl-4-piperidinyl)-3-triisopropylsilyl-2-propyn-1-ol

Conditions

Conditions	Yield
With (αR,2S)-(-)-1-(2-diphenylphosphinobenzyl)-α-(2,2-dimethylpropynyl)-2-pyrrolidinemethanol; copper (I) tert-butoxide In tert-butyl alcohol at 25℃; for 72h; Inert atmosphere; enantioselective reaction;	99%

: 22065-85-6
1-benzyl-4-formylpiperidine

: 75-52-5
nitromethane

: C14H20N2O3

Conditions

Conditions	Yield
With potassium fluoride In isopropyl alcohol at 20℃;	96%

: 22065-85-6
1-benzyl-4-formylpiperidine

: 2398-37-0
3-methoxyphenyl bromide

: 255723-94-5
N-benzyl-4-[hydroxy(3-methoxyphenyl)methyl]piperidine

Conditions

Conditions	Yield
Stage #1: 3-methoxyphenyl bromide With magnesium In tetrahydrofuran for 0.5h; Grignard reaction; Heating; Stage #2: N-benzyl-4-formylpiperidine In tetrahydrofuran at 20℃; for 2h; Addition;	94.3%

: 2107-69-9
5,6-dimethoxy-1-indanone

: 22065-85-6
1-benzyl-4-formylpiperidine

: (E)-2-((1-benzylpiperidine-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 0 - 25℃; for 1.25h; Product distribution / selectivity;	92.2%
With sodium methylate In isopropyl alcohol at 0 - 25℃; for 3.25h; Product distribution / selectivity;	92.5%
With tetrabutylammomium bromide; potassium hydroxide In dichloromethane; water at 38℃; for 1.5h;	90%

: 22065-85-6
1-benzyl-4-formylpiperidine

: 2942-58-7
diethyl cyanophosphonate

: 2408-36-8
lithium cyanide

: (1-benzylpiperidin-4-yl)cyanomethyl diethylphosphate

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h;	92%

...Expand

: 2107-69-9
5,6-dimethoxy-1-indanone

: 22065-85-6
1-benzyl-4-formylpiperidine

: 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine hydrochloride

Conditions

Conditions	Yield
Stage #1: 5,6-dimethoxy-1-indanone; N-benzyl-4-formylpiperidine In dichloromethane at 25 - 30℃; Stage #2: With potassium hydroxide In methanol; dichloromethane at 0 - 30℃;	91.3%

: 20077-92-3
2-methylbenzothiazol-5-yl methyl ketone

: 22065-85-6
1-benzyl-4-formylpiperidine

: 3-(1-benzylpiperidin-4-yl)-3-hydroxy-1-(2-methylbenzothiazol-6-yl)propan-1-one

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.75h;	90%

: 22065-85-6
1-benzyl-4-formylpiperidine

: 873-77-8
(4-chlorphenyl)magnesium bromide

: 1226878-35-8
(1-benzylpiperidin-4-yl)(4-chlorophenyl)methanol

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.55h; Grignard reaction; Inert atmosphere;	90%

: 1067-71-6
Diethyl (2-oxopropyl)phosphonate

: 22065-85-6
1-benzyl-4-formylpiperidine

: 1335032-58-0
(E)-4-(1-benzylpiperidin-4-yl)but-3-en-2-one

Conditions

Conditions	Yield
Stage #1: Diethyl (2-oxopropyl)phosphonate With potassium carbonate In tetrahydrofuran at 20℃; for 0.583333h; Reflux; Stage #2: N-benzyl-4-formylpiperidine In tetrahydrofuran for 3h; Wittig reaction; Reflux;	90%

: 22065-85-6
1-benzyl-4-formylpiperidine

: 137013-02-6
5,6-Diethoxy-1-indanone

: 1-benzyl-4-[(5,6-diethoxy-1-indanon)-2-ylidene]methylpiperidine

Conditions

Conditions	Yield
With sodium methylate In tetrahydrofuran; methanol; water for 2h;	89%

: 22065-85-6
1-benzyl-4-formylpiperidine

: 4693-38-3
3-chloro-1-(3,4-dimethoxyphenyl)propan-1-one

: 120014-07-5
1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine

Conditions

Conditions	Yield
With triethylammonium tetrachloroaluminate at 55 - 175℃; for 11h; Temperature; Reagent/catalyst; Concentration; Inert atmosphere;	89%

: 2107-69-9
5,6-dimethoxy-1-indanone

: 22065-85-6
1-benzyl-4-formylpiperidine

: 120014-06-4
donepezil

Conditions

Conditions	Yield
With aluminum oxide; Pt/Al2O3 In tetrahydrofuran; ethanol; water; isopropyl alcohol at 45 - 55℃; for 7h; Temperature; Solvent; Reagent/catalyst; Aldol Condensation;	88%
Multi-step reaction with 2 steps 1: sodium methylate / tetrahydrofuran 2: palladium 10% on activated carbon; hydrogenchloride / ethanol; water View Scheme

: 22065-85-6
1-benzyl-4-formylpiperidine

: (4-iodo-5-methoxypyrrolo[2,3-b]pyridin-1-yl)triisopropylsilane

: (1-benzyl-4-piperidyl)-(5-methoxy-1-triisopropylsilylpyrrolo[2,3-b]pyridin-4-yl)methanol

Conditions

Conditions	Yield
Stage #1: (4-iodo-5-methoxypyrrolo[2,3-b]pyridin-1-yl)triisopropylsilane With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.666667h; Stage #2: N-benzyl-4-formylpiperidine In tetrahydrofuran at 0℃; for 1h;	84.8%

: 22065-85-6
1-benzyl-4-formylpiperidine

: diethyl ((6-((2-methyl-1-oxo-1-(phenylamino)propan-2-yl)oxy)quinolin-2-yl)methyl)phosphonate

: (E)-2-((3-(2-(1-benzylpiperidin-4-yl)vinyl)isoquinolin-7-yl)oxy)-2-methyl-N-phenylpropanamide

Conditions

Conditions	Yield
Stage #1: diethyl ((6-((2-methyl-1-oxo-1-(phenylamino)propan-2-yl)oxy)quinolin-2-yl)methyl)phosphonate With n-butyllithium In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: N-benzyl-4-formylpiperidine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	84%

: 22065-85-6
1-benzyl-4-formylpiperidine

: 50586-62-4
diethyl cyanomethyl phosphonate

: 151097-69-7
(2E)-3-(1-benzylpiperidin-4-yl)prop-2-enenitrile

Conditions

Conditions	Yield
Stage #1: diethyl cyanomethyl phosphonate With potassium carbonate In tetrahydrofuran at 20℃; for 0.5h; Reflux; Stage #2: N-benzyl-4-formylpiperidine In tetrahydrofuran for 12h; Reflux;	83%

: 2107-69-9
5,6-dimethoxy-1-indanone

: 22065-85-6
1-benzyl-4-formylpiperidine

: 197010-20-1
2-((1-benzyl-piperidin-4-yl)-hydroxymethyl)-5,6-dimethoxyindan-1-one

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In water; toluene for 4h; Reflux; Large scale;	81.29%

: 1452-63-7
picolinic acid hydrazide

: 22065-85-6
1-benzyl-4-formylpiperidine

: (E)-N'-((1-benzylpiperidin-4-yl)methylene)picolinohydrazide

Conditions

Conditions	Yield
In methanol at 100℃; for 0.5h; Microwave irradiation;	80%

: 22065-85-6
1-benzyl-4-formylpiperidine

: 371-67-5
2,2,2-trifluorodiazoethane

: 109-73-9
N-butylamine

: 1-benzyl-4-(1-butyl-4-(trifluoromethyl)-4,5-dihydro-1H-1,2,3-triazol-5-yl)piperidine

Conditions

Conditions	Yield
With silver carbonate In toluene at 25℃; for 8h; diastereoselective reaction;	79%

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: 22065-85-6
1-benzyl-4-formylpiperidine

: 89302-81-8
(3-fluorobenzyl)(triphenyl)phosphonium bromide

: (E)-1-benzyl-4-(3-fluorostyryl)piperidine

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Cooling with ice;	78.1%

: 22065-85-6
1-benzyl-4-formylpiperidine

: 2747-08-2
2-bromo-5,6-dimethoxy-1-indanone

: (E)-2-((1-benzylpiperidine-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Conditions

Conditions	Yield
With 1-phenylphospholane-1-oxide; diphenylsilane; N-ethyl-N,N-diisopropylamine In toluene at 100℃; for 24h; Wittig Olefination; Inert atmosphere;	76%

: 22065-85-6
1-benzyl-4-formylpiperidine

: 473659-21-1
diethyl (1-tritylimidazol-4-yl)methylphosphonate

: (E)-1-benzyl-4-(1-triphenylmethylimidazol-4-ylethylene)piperidine

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 2h; Horner-Wadsworth-Emmons reaction; Heating;	74%
With potassium tert-butylate In tetrahydrofuran for 2h; Heating / reflux;	74%

N-Benzylpiperidine-4-carboxaldehyde Chemical Properties

Molecular Structure of N-Benzylpiperidine-4-carboxaldehyde (CAS NO.22065-85-6):

IUPAC Name: 1-benzylpiperidine-4-carbaldehyde
Empirical Formula: C₁₃H₁₇NO
Molecular Weight: 203.2802
EINECS: 244-757-7
Sensitive: Air Sensitive
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 20.31 Å²
Index of Refraction: 1.6
Molar Refractivity: 62.4 cm³
Molar Volume: 182.3 cm³
Surface Tension: 51.1 dyne/cm
Density: 1.114 g/cm³
Flash Point: 104.3 °C
Enthalpy of Vaporization: 53.95 kJ/mol
Boiling Point: 299.5 °C at 760 mmHg
Vapour Pressure: 0.00119 mmHg at 25°C
InChI
InChI=1/C13H17NO/c15-11-13-6-8-14(9-7-13)10-12-4-2-1-3-5-12/h1-5,11,13H,6-10H2
Smiles
N1(Cc2ccccc2)CCC(C=O)CC1
Product Categories: pharmacetical; Alcohol Aldehyde & acid series; Piperidine; (intermediate of donepezil); Aromatics; Heterocycles; Building Blocks; Heterocyclic Building Blocks; Piperidines

N-Benzylpiperidine-4-carboxaldehyde Safety Profile

Hazard Codes: Toxic T
Risk Statements: 25-41
R25 :Toxic if swallowed.
R41:Risk of serious damage to the eyes.
Safety Statements: 26-28-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28:After contact with skin, wash immediately with plenty of soap-suds.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2810 6.1/PG 3
WGK Germany: 3
HazardClass: Irritant

N-Benzylpiperidine-4-carboxaldehyde Specification

N-Benzylpiperidine-4-carboxaldehyde , with CAS number of 22065-85-6, can be called 4-piperidinecarboxaldehyde, 1-(phenylmethyl)- ; 1-Benzylpiperidin-4-carbaldehyd ; 1-Benzylpiperidine-4-carbaldehyde ; 1-Benzyl-4-piperidinecarboxaldehyde ; 1-Benzyl-4-piperidine-carboxaldehyde ; N-BenzylpiperN-Benzylpiperidine-4-carboxaldehyde . It is a kind of colorless oil.

Product Name

N-Benzylpiperidine-4-carboxaldehyde

Synthetic route

N-Benzylpiperidine-4-carboxaldehyde Chemical Properties

N-Benzylpiperidine-4-carboxaldehyde Safety Profile

N-Benzylpiperidine-4-carboxaldehyde Specification

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