HCID 178424364, compound → 2-methyl-N-[(1R)-1-phenylethyl]cyclohexan-1-amine

HRID 62659Notes

Reaction equation

HRID 62659 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4]/[C:3]/1=[N:8]\[C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10]>C(O)C.[Ni]>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][C@@H:9]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:10]

Participants

4

Reactant 1

HCID 178424364HCID 178424364, compound

Product 1

HCID 127142172-methyl-N-[(1R)-1-phenylethyl]cyclohexan-1-amineYield 80%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of (1R,E)-N-(2-methylcyclohexylidene)-1-phenylethanamine (I-8a: 25 g, 116.27 mmol) and Raney-Ni (3.75 g) in ethanol (250 mL) was maintained under hydrogen atmosphere in a Parr hydrogenator using 5 bar pressure for 2 days. The reaction mixture was filtered and filtrate evaporated under reduced pressure. The crude compound was treated with ethereal HCl, and the precipitated salt was filtered, washed with cold ether and dried to afford 20 g (80%) of 2-methyl-N—((R)-1-phenylethyl)-cyclohexanamine (I-8b) as a white solid.

Workup

  1. temperaturewas maintained under hydrogen atmosphere in a Parr hydrogenator
  2. customfor 2 days
  3. filtrationThe reaction mixture was filtered
  4. customfiltrate evaporated under reduced pressure
  5. additionThe crude compound was treated with ethereal HCl
  6. filtrationthe precipitated salt was filtered
  7. washwashed with cold ether
  8. customdried

Sources & evidence

ORD record
ord-350460199f344be4b1b3c00607a63c82
Source dataset
uspto-grants-2016_09
Patent number
US09447039B2

Reaction notes

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