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

HRID 1757409Notes

Reaction equation

HRID 1757409 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. 1H-NMR (250 MHz, CDCl3): δ=1.68-1.75 (2H, br. s), 1.83-1.97 (1H, m), 2.27-2.41 (1H, m), 2.51 (1H, dd, J=9.0, 8.1 Hz), 2.71 (1H, td, J=8.9, 5.9 Hz), 2.80-2.90 (1H, m), 3.01-3.08 (1H, m), 3.31-3.41 (1H, m), 3.69 (2H, AB quartet, JAB =13.3 Hz), 3.84 (2H, s), 7.11-7.39 (9H, m).

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-b3d9a20e926841c6bfb99f1c6602f71f
Source dataset
uspto-grants-1995_08
Patent number
US05446044

Reaction notes

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