Aniline → 3-Piperidinamine, N-phenyl-1-(phenylmethyl)-

HRID 1246925

Reaction equation

HRID 1246925 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH3-]C#N.[Na+].[OH-].[K+]>CO.O>[CH2:2]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 14797Potassium HydroxideHCID 30849241-Benzyl-3-piperidone hydrochloride hydrateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 113914823-Piperidinamine, N-phenyl-1-(phenylmethyl)-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-benzyl-piperidin-3-one hydrochloride salt (2.02 g, 8.95 mmol), aniline (1.67 ml, 17.89 mmol) in MeOH (20 ml) at room temperature was added NaCNBH3 (1.8 g, 28.64 mmol) in several portions. The mixture was stirred over night. The mixture was taken up in 50 ml of water, the pH was increased to 12 with 2N KOH and extracted with CH2Cl2 (3×50 ml). Standard work-up of the organic solution provided 164 as a dried residue which was used in the next step without further purification. LRMS (calculated for C18H22N2) 266. found 266.

Workup

  1. extractionextracted with CH2Cl2 (3×50 ml)

Sources & evidence

ORD record
ord-40c04b082f374f178bb5831264c79802
Source dataset
uspto-grants-2006_10
Patent number
US07129228B2

Linked notes

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