Ammonia → 3-[1-(Phenylmethyl)-3-pyrrolidinyl]benzenemethanamine

HRID 1742844Notes

Reaction equation

HRID 1742844 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[C:16]#[N:17])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N>[Ni].CO>[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:14]=[C:15]([CH2:16][NH2:17])[CH:18]=[CH:19][CH:20]=3)[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 199590113-[1-(Phenylmethyl)-3-pyrrolidinyl]benzonitrile

Product 1

HCID 199590393-[1-(Phenylmethyl)-3-pyrrolidinyl]benzenemethanamineYield 84%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3-[1-(phenylmethyl)-3-pyrrolidinyl]benzonitrile (11.90 g, 45.4 mmol) and Raney nickel (5.0 g) in methanol saturated with ammonia (100 mL) was hydrogenated in a Parr shaker at 3 atm. The resulting suspension was filtered through a pad of Celite and the filtrate concentrated to give an off-green liquid. This crude product was chromatographed (silica gel, chloroform-methanol 2:1) to give the title compound (10.12 g, 84%) as a colorless oil.

Workup

  1. filtrationThe resulting suspension was filtered through a pad of Celite
  2. concentrationthe filtrate concentrated
  3. customto give an off-green liquid
  4. customThis crude product was chromatographed (silica gel, chloroform-methanol 2:1)

Sources & evidence

ORD record
ord-e7be340cf8844eaab35590c8d8109617
Source dataset
uspto-grants-1994_08
Patent number
US05342844

Reaction notes

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