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

HRID 479830Notes

Reaction equation

HRID 479830 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-daf9308aa91646018dc0d82c8883586c
Source dataset
uspto-grants-2003_11
Patent number
US06645980B1

Reaction notes

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