Ammonia → HCID 86716214, compound

HRID 512186Notes

Reaction equation

HRID 512186 reaction equation
[F:1][C:2]1([F:19])[CH2:7][CH2:6][C:5](/[C:15](=[N:17]\O)/[CH3:16])([C:8]2[CH:9]=[N:10][C:11]([CH3:14])=[N:12][CH:13]=2)[CH2:4][CH2:3]1.N>[Ni]>[F:19][C:2]1([F:1])[CH2:3][CH2:4][C:5]([CH:15]([NH2:17])[CH3:16])([C:8]2[CH:13]=[N:12][C:11]([CH3:14])=[N:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 117870451HCID 117870451, compound

Product 1

HCID 86716214HCID 86716214, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of (Z)-1-(4,4-difluoro-1-(2-methylpyrimidin-5-yl)cyclohexyl)ethanone oxime (320 mg, 1.19 mmol) and aq.NH3 (2 mL) was hydrogenated with Raney Ni (300 mg) under H2 (50 Psi) for 3 h. The reaction mixture was filtered and concentrated. The residue was dissolved in EtOAc (15 mL), dried over Na2SO4 and concentrated to give 1-(4,4-difluoro-1-(2-methylpyrimidin-5-yl)cyclohexyl)ethanamine (300 mg), which was used for the next step directly.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc (15 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1448857e73354cca8e2fabf8f3dd60cf
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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