3-(Trifluoromethyl)aniline → HCID 12298118, compound

HRID 1973812Notes

Reaction equation

HRID 1973812 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=1.[C-:26]#[N:27].[K+].[OH-].[NH4+]>C(O)(=O)C>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11]([NH:23][C:19]3[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:24])([F:25])[F:15])[CH:18]=3)([C:26]#[N:27])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 9032Potassium CyanideHCID 14923Ammonium HydroxideHCID 192201-Benzyl-4-piperidone

Product 1

HCID 12298118HCID 12298118, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 378.5 parts of 1-(phenylmethyl)-4-piperidinone and 362.5 parts of 3-(trifluoromethyl)benzenamine in 1500 parts of acetic acid is stirred for 1 hour at room temperature: exothermic reaction (temperature rises to 40° C). After cooling, there are added 262.7 parts of potassium cyanide and the whole is stirred for 4 days at room temperature. The reaction mixture is poured onto a mixture of crushed ice and ammonium hyroxide and the product is extracted with trichloromethane. The extract is washed with a diluted ammonium hydroxide solution, dried, filtered and evaporated. The residue is crystallized from a mixture of 2,2'-oxybispropane and petroleum-ether (2:1 by volume), yielding 1-(phenylmethyl)-4-{[3-(trifluoromethyl)phenyl]amino}-4-piperidinecarbonitrile; mp. 96° C.

Workup

  1. customexothermic reaction (temperature rises to 40° C)
  2. temperatureAfter cooling
  3. extractionthe product is extracted with trichloromethane
  4. washThe extract is washed with a diluted ammonium hydroxide solution
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from a mixture of 2,2'-oxybispropane and petroleum-ether (2:1 by volume)

Sources & evidence

ORD record
ord-1f848ddd8adf42b4b0f39ae41951c0c1
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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