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inquiry3-(dimethylamino)propiophenone hydrochloride
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate; sodium hydroxide at 20℃; for 1h; pH=12 - 13; Cooling with ice; | 96% |
Stage #1: 3-(dimethylamino)propiophenone hydrochloride With potassium hydroxide In water Stage #2: With methanol; sodium tetrahydroborate; potassium hydroxide at 0 - 22℃; for 1.5h; | 95% |
With diisobutylaluminium hydride In tetrahydrofuran; dichloromethane for 2h; Ambient temperature; | 92% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In water at 0 - 20℃; | 91% |
With lithium aluminium tetrahydride | |
With aluminium trichloride; aluminum isopropoxide; isopropyl alcohol |
N,N-Dimethyl-α-chlorobenzoylacetamide
A
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
(+/-)-N-methylephedrine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether for 20h; Heating; | A n/a B 24% |
3-chloro-1-phenyl-propan-1-ol
dimethyl amine
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
styrene
N-(chloromethyl)dimethylamine
A
2-benzyl-2-propenal
B
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
C
methyl-(3-phenyl-propyl)-amine
D
bis-(3-phenyl-propyl)-amine
Conditions | Yield |
---|---|
In acetonitrile for 12h; Heating; Yield given. Further byproducts given. Yields of byproduct given; |
diethyl ether
water
3-dimethylaminopropiophenone
A
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
Conditions | Yield |
---|---|
With water; palladium Hydrogenation; |
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
Conditions | Yield |
---|---|
With water; nickel Hydrogenation; |
3-(dimethylamino)propiophenone hydrochloride
water
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
Conditions | Yield |
---|---|
Hydrogenation; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 83 percent / aq. HCl / ethanol / 2 h / Heating 2: 91 percent / NaBH4 / H2O / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol; water / 3 h / Heating / reflux 2: sodium tetrahydroborate / ethanol / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethanol / 2 h / Reflux 2.1: potassium hydroxide / water 2.2: 1.5 h / 0 - 22 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 84 percent / conc. aq. HCl / ethanol / 2 h / Heating 2: 92 percent / DIBAL-H / tetrahydrofuran; CH2Cl2 / 2 h / Ambient temperature View Scheme |
N,N-dimethyl 3-oxo-3-phenyl-propanamide
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 81 percent / N-chlorosuccinimide / CCl4 / 4 h / Heating 2: LiAlH4 / diethyl ether / 20 h / Heating View Scheme |
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
Conditions | Yield |
---|---|
With sodium borohydrid In methanol; water; isopropyl alcohol | 15.2 g (97%) |
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
3-(dimethylamino)-1-phenylpropyl chloride hydrochloride
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With hydrogenchloride In diethyl ether Stage #2: With thionyl chloride Reflux; | 96% |
With hydrogenchloride; thionyl chloride In dichloromethane | |
With thionyl chloride In dichloromethane |
5-bromo-2-chloropyridine
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
3-((5-bromopyridin-2-yl)oxy)-N,N-dimethyl-3-phenylpropan-1-amine
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: 5-bromo-2-chloropyridine In N,N-dimethyl-formamide; mineral oil at 75℃; for 12h; | 91% |
4-nitro-1H-pyrazole
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
N,N-dimethyl-3-(4-nitro-1H-pyrazol-1-yl)-3-phenylpropan-1-amine
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; | 80% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement; |
4-nitro-phenol
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
N,N-dimethyl-3-(4-nitrophenoxy)-3-phenylpropan-1-amine
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Mitsunobu Displacement; | 80% |
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 48h; Mitsunobu Displacement; |
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
6-[1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]-1-(2-trimethylsilanylethoxymethyl)-1H-indazole-3-carboxylic acid (1H-pyrazol-4-yl)amide
Conditions | Yield |
---|---|
With tributylphosphine; diethylazodicarboxylate In tetrahydrofuran at 70℃; for 1h; | 75% |
1-indoline
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
N-[3-(2,3-dihydro-1H-indol-1-yl)-3-phenylpropyl]-N,N-dimethylamine
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 1-indoline With potassium carbonate at 20℃; for 14h; Further stages.; | 72% |
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile Stage #2: phenol With potassium carbonate In acetonitrile for 65h; Heating; | 69% |
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 3,4-dimethoxyphenol With potassium carbonate In acetonitrile for 16h; Heating; | 67% |
6-fluoroindoline
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
C19H23N2F
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 6-fluoroindoline With potassium carbonate at 20℃; for 14h; Further stages.; | 64% |
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
3-chloro-N,N-dimethyl-3-phenylpropan-1-amine
Conditions | Yield |
---|---|
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; | 64% |
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
2-fluoro-1,4-dimethoxybenzene
[3-(2,5-dimethoxy-phenoxy)-3-phenylpropyl]dimethylamine
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 2-fluoro-1,4-dimethoxybenzene In dimethyl sulfoxide at 135 - 140℃; for 4h; | 63% |
6-chloropyridine-3-ol
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
3-((6-chloropyridin-3-yl)oxy)-N,N-dimethyl-3-phenylpropan-1-amine
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement; Inert atmosphere; | 60% |
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
2,3-dihydro-4-fluoro-1H-indole
C19H23N2F
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 2,3-dihydro-4-fluoro-1H-indole With potassium carbonate at 20℃; for 14h; Further stages.; | 51% |
5-fluoroindoline
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
C19H23N2F
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 5-fluoroindoline With potassium carbonate at 20℃; for 14h; Further stages.; | 49% |
2,3-dihydro-7-fluoro-1H-indole
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
C19H23N2F
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 2,3-dihydro-7-fluoro-1H-indole With potassium carbonate at 20℃; for 14h; Further stages.; | 47% |
O-methylresorcine
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
[3-(3-methoxy-phenoxy)-3-phenyl-propyl]-dimethyl-amine
Conditions | Yield |
---|---|
With PS-PPh3; dibenzyl azodicarboxylate In dichloromethane at 20℃; for 20h; Mitsunobu reaction; | 47% |
4-fluorobenzo[1,3]dioxolane
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
oxalic acid
Conditions | Yield |
---|---|
Stage #1: 4-fluorobenzo[1,3]dioxolane; N,N-dimethyl-3-hydroxy-3-phenylpropylamine With potassium hydroxide In dimethyl sulfoxide at 85℃; for 4h; Stage #2: oxalic acid | 47% |
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 4-methoxy-phenol With potassium carbonate In acetonitrile for 16h; Heating; | 46% |
4-hydroxybenzotrifluoride
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
N,N-dimethyl-3-phenyl-3-(4-(trifluoromethyl)phenoxy)-1-propylamine
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 4-hydroxybenzotrifluoride With potassium carbonate In acetonitrile for 16h; Heating; | 35% |
4-(3-piperidin-1-yl-propoxy)-phenol
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
Conditions | Yield |
---|---|
With PS-PPh3; dibenzyl azodicarboxylate In dichloromethane at 20℃; for 20h; Mitsunobu reaction; | 10% |
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
2-chloro-2,2-diphenylacetyl chloride
benzilic acid-(3-dimethylamino-1-phenyl-propyl ester)
Conditions | Yield |
---|---|
With diethyl ether Erhitzen des Reaktionsprodukts mit Wasser; |
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
benzoic acid-(3-dimethylamino-1-phenyl-propyl ester)
Conditions | Yield |
---|---|
With benzoyl chloride In 1,4-dioxane at 25 - 50℃; Kinetics; |
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
benzoyl chloride
benzoic acid-(3-dimethylamino-1-phenyl-propyl ester)
Conditions | Yield |
---|---|
In benzene |
N,N-dimethyl-3-hydroxy-3-phenylpropylamine
methyl iodide
3-Hydroxy-3-phenylpropyltrimethylammoniumiodid
Conditions | Yield |
---|---|
In ethanol for 0.666667h; Heating; Yield given; |
Conditions | Yield |
---|---|
In ethyl acetate 77 deg C, 1 h and -15 deg C, 1 h; Yield given; |
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