Sodium Carbonate → HCID 20366934, compound

HRID 617001

Reaction equation

HRID 617001 reaction equation
S(C1C=CC(C)=CC=1)(O[CH:5]1[CH2:10][CH2:9][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=O)=[O:2].[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2([OH:43])[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[CH:33][C:32]=1[C:44]([F:47])([F:46])[F:45].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[OH2:2].[ClH:30].[C:11]1([C:8]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:7][CH2:6][CH:5]([N:40]3[CH2:39][CH2:38][C:37]([C:34]4[CH:35]=[CH:36][C:31]([Cl:30])=[C:32]([C:44]([F:47])([F:45])[F:46])[CH:33]=4)([OH:43])[CH2:42][CH2:41]3)[CH2:10][CH2:9]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 891074-(4-Chloro-3-(trifluoromethyl)phenyl)piperidin-4-olHCID 20366912807-24-9

Product 1

HCID 20366934HCID 20366934, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4.1 g of 4,4-diphenylcyclohexyl tosylate, 2.8 g of 4-(4-chloro-3-trifluoromethylphenyl)-4-piperidinol, 1.1 g of sodium carbonate and 400 ml of toluene is stirred under reflux for 48 hours. The reaction mixture is concentrated completely under reduced pressure, water is added to the residue, and the aqueous mixture is extracted with chloroform. The extract is washed with water and dried over sodium sulfate, and the solvent is removed. The esidual viscous oil is purified by column chromatography on silica gel using chloroform and then chloroform - methanol (9:1) as an eluent. The purified base is converted in a conventional manner into the hydrochloride. Thus is obtained 1-(4,4-diphenylcyclohexyl)-4-(4-chloro-3-trifluoromethylphenyl)-4-piperidinol hydrochloride monohydrate as white crystals, melting at 270°-273° C.

Workup

  1. temperatureunder reflux for 48 hours
  2. concentrationThe reaction mixture is concentrated completely under reduced pressure, water
  3. additionis added to the residue
  4. extractionthe aqueous mixture is extracted with chloroform
  5. washThe extract is washed with water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is removed
  8. customThe esidual viscous oil is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6b2e2ad3436c4cc69ba735545e7b983b
Source dataset
uspto-grants-1978_02
Patent number
US04076821

Linked notes

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