Ammonium Hydroxide → 2-Phenoxy-6-(1-piperidinyl)benzenemethanamine

HRID 1499115Notes

Reaction equation

HRID 1499115 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:9]=1[C:10]#[N:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[OH-]>CO.[Ni]>[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:9]=1[CH2:10][NH2:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 1179420612-phenoxy-6-(1-piperidinyl)Benzonitrile

Product 1

HCID 1179477812-Phenoxy-6-(1-piperidinyl)benzenemethanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To 2-phenoxy-6-(piperidin-1-yl)benzonitrile (250 mg, 0.9 mmol) from Step 1 in 20 mL of MeOH was added Raney Nickel (5%) and NH4OH (2 mL). The reaction was stirred under 1 atm of H2 at RT for 2 h. The solid was filtered away and the filtrate was concentrated in vacuo to provide the title compound as a viscous oil.

Workup

  1. filtrationThe solid was filtered away
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c9b29aec1d474c0a9c8206a3d9ed77c6
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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