Ammonia → HCID 20278960, compound

HRID 1156319Notes

Reaction equation

HRID 1156319 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH:14]([CH3:17])[C:15]#[N:16])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.N.[H][H]>[Ni].CO>[NH2:16][CH2:15][CH:14]([N:11]1[CH2:12][CH2:13][CH:8]([C:6]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:19][CH:18]=2)=[O:7])[CH2:9][CH2:10]1)[CH3:17]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 134765514-(4-Fluorobenzoyl)-alpha-methyl-1-piperidineacetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 20278960HCID 20278960, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 32 parts of 4-(4-fluorobenzoyl)-α-methyl-1-piperidineacetonitrile and 400 parts of methanol, saturated with ammonia is hydrogenated in the Parr-apparatus at 25° C. with 5 parts of Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is taken up in methylbenzene and the latter is evaporated again. The residue is dissolved in 2,2'-oxybispropane and the solution is filtered till clear. The solvent is evaporated, yielding 32 parts (100%) of [1-(2-amino-1-methylethyl)-4-piperidinyl] (4-fluorophenyl)methanone as an oily residue.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customthe latter is evaporated again
  4. dissolutionThe residue is dissolved in 2,2'-oxybispropane
  5. filtrationthe solution is filtered till clear
  6. customThe solvent is evaporated

Sources & evidence

ORD record
ord-82b236396d184543a936b2bc844e477c
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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