Aniline → HCID 13364167, compound

HRID 616998Notes

Reaction equation

HRID 616998 reaction equation
[C-:1]#[N:2].[K+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:16][CH2:15][CH:14]([N:17]3[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)(=O)C>[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:16][CH2:15][CH:14]([N:17]3[CH2:22][CH2:21][C:20]([C:1]#[N:2])([NH:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 9032Potassium CyanideHCID 11430Potassium CarbonateHCID 133641261-(1~4~,3~4~-Difluoro[2~3~,2~4~,2~5~,2~6~-tetrahydro-2~2~H-[1~1~,2~1~:2~1~,3~1~-terphenyl]]-2~4~-yl)piperidin-4-one

Product 1

HCID 13364167HCID 13364167, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2.9 g of potassium cyanide in 8 ml of water is added dropwise to a mixture of 16.3 g of 1-[4,4-bis(p-fluorophenyl)cyclohexyl]-4-piperidone (oil; its hydrochloride: m.p. 214°-217° C), 4.1 g of aniline and 40 ml of acetic acid at room temperature with stirring. The resulting mixture is stirred at room temperature for 6 hours and allowed to stand at room temperature overnight. The reaction mixture is poured into ice water, the aqueous mixture is made alkaline with potassium carbonate, and the alkaline mixture is extracted with chloroform. The extract is washed with water and dried over sodium sulfate, and the solvent is removed. The residual oil is dissolved in acetone, and 20% ethanolic hydrochloric acid is added thereto. After cooling the precipitated hydrochloride is collected by filtration and converted in a conventional manner into the base. The obtained crystals are recrystallized from a mixture of acetone and petroleum ether to give 1-[4,4-bis(p-fluorophenyl)cyclohexyl]-4-cyano-4-anilinopiperidine as white crystals, melting at 139° -140° C.

Workup

  1. stirringThe resulting mixture is stirred at room temperature for 6 hours
  2. extractionthe alkaline mixture is extracted with chloroform
  3. washThe extract is washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is removed
  6. dissolutionThe residual oil is dissolved in acetone
  7. addition20% ethanolic hydrochloric acid is added
  8. temperatureAfter cooling the precipitated hydrochloride
  9. filtrationis collected by filtration
  10. customThe obtained crystals are recrystallized from a mixture of acetone and petroleum ether

Sources & evidence

ORD record
ord-b3c57959aee44e70a9c2b1f214b4daf4
Source dataset
uspto-grants-1978_02
Patent number
US04076821

Reaction notes

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