HCID 76545195, compound → HCID 22456855, compound

HRID 2186513Notes

Reaction equation

HRID 2186513 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15](=[N:17]O)[CH3:16])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.N.[Ni]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH3:16])[NH2:17])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 76545195HCID 76545195, compound

Product 1

HCID 22456855HCID 22456855, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A solution of 1-[3-(cyclopentyloxy)-4-methoxyphenyl]ethanone oxime (15.3 g) in methanol/ammonia (350 ml) was hydrogenated for 3 hours with Raney nickel (3 g) as a catalyst. After uptake of H2, the catalyst was filtered off, washed with methanol and the filtrate was evaporated. Toluene was added and azeotroped on the rotary evaporator, yielding 14.45 g (100%) of (±)-3-(cyclopentyloxy)-4-methoxy-α-methylbenzenemethanamine (interm. 5).

Workup

  1. filtrationAfter uptake of H2, the catalyst was filtered off
  2. washwashed with methanol
  3. customthe filtrate was evaporated
  4. additionToluene was added
  5. customazeotroped on the rotary evaporator

Sources & evidence

ORD record
ord-e39df145baeb45389154907e7da056e9
Source dataset
uspto-grants-2002_06
Patent number
US06403805B1

Reaction notes

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