4-Benzylmorpholine-2-carbonitrile → (4-Benzylmorpholin-2-yl)methanamine

HRID 2364671Notes

Reaction equation

HRID 2364671 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]#[N:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Ni]>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][NH2:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 156511954-Benzylmorpholine-2-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 2776360(4-Benzylmorpholin-2-yl)methanamineYield 72.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4-benzylmorpholine-2-carbonitrile 2c (0.80 g, 4 mmol) was dissolved in 30 mL of methanol followed by the addition of Raney nickel (0.50 g), filled with hydrogen two times and the resulting solution was stirred for 12 hours, filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound (4-benzylmorpholin-2-yl)methanamine 2d (0.60 g) as a colorless oil liquid, which was used in the next step without further furification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f6153a9df3fb43ed92cc10f82fbc9df2
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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