Ammonia → 2-[3-Methoxy-4-(3-phenyl-propoxy)-phenyl]-ethylamine

HRID 1862640Notes

Reaction equation

HRID 1862640 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][C:20]#[N:21])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N>CO.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][CH2:20][NH2:21])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 18619867[3-Methoxy-4-(3-phenyl-prop-2-ynyloxy)-phenyl]-acetonitrile

Product 1

HCID 186201942-[3-Methoxy-4-(3-phenyl-propoxy)-phenyl]-ethylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of [3-methoxy-4-(3-phenyl-prop-2-ynyloxy)-phenyl]-acetonitrile (2.0 g), liquid ammonia (5 g) and Raney-nickel (1 g) in methanol (100 ml) is shaken in an autoclave under hydrogen (100 bar) at +70° C. for 2 hours. The reaction mixture is filtered and evaporated. 2-[3-Methoxy-4-(3-phenyl-propoxy)-phenyl]-ethylamine is obtained as an oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated

Sources & evidence

ORD record
ord-b52a415ee6d844c98cf5d47f5f538a9a
Source dataset
uspto-grants-2003_03
Patent number
US06538159B2

Reaction notes

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