Sulfuric Acid → HCID 13364168, compound

HRID 616999Notes

Reaction equation

HRID 616999 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:13][CH2:12][CH:11]([N:14]3[CH2:19][CH2:18][C:17]([C:27]#[N:28])([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:37]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[CH2:9][CH2:10][CH:11]([N:14]3[CH2:19][CH2:18][C:17]([C:27](=[O:37])[NH2:28])([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 13364167HCID 13364167, compound

Product 1

HCID 13364168HCID 13364168, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

To 16.5 g of 1-[4,4-bis(p-fluorophenyl)cyclohexyl]-4-cyano-4-anilinopiperidine is added gradually a solution of 180 g of concentrated sulfuric acid and 20 ml of water under cooling. After the addition is complete, the resulting mixture is stirred at 70° C for 1 hour and then cooled. The reaction mixture is poured into water, and the precipitated powder is collected by filtration. Then water is added to the powder, the aqueous mixture is made alkaline with potassium carbonate, and the alkaline solution is extracted with chloroform. The extract is washed with water and dried over sodium sulfate, and the solvent is removed. The precipitated crystals are collected by filration and recrystallized from a mixture of chloroform and acetone to give 1-[4,4-bis(p-fluorophenyl)cyclohexyl]-4-carbamoyl-4-anilinopiperidine as white crystals, melting at 224°-227° C.

Workup

  1. temperatureunder cooling
  2. additionAfter the addition
  3. temperaturecooled
  4. filtrationthe precipitated powder is collected by filtration
  5. additionThen water is added to the powder
  6. extractionthe alkaline solution is extracted with chloroform
  7. washThe extract is washed with water
  8. dry with materialdried over sodium sulfate
  9. customthe solvent is removed
  10. customThe precipitated crystals are collected by filration
  11. customrecrystallized from a mixture of chloroform and acetone

Sources & evidence

ORD record
ord-a7e9cd825f2c49b6b281ffead20b66a1
Source dataset
uspto-grants-1978_02
Patent number
US04076821

Reaction notes

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