Potassium Carbonate → HCID 20366938, compound

HRID 616991Notes

Reaction equation

S(C1C=CC(C)=CC=1)(O[CH:5]1[CH2:9][CH2:8][C:7]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:6]1)(=O)=O.Cl.[NH:32]1[CH2:37][CH2:36][CH:35]([N:38]2[C:42]3[CH:43]=[CH:44][C:45]([Cl:47])=[CH:46][C:41]=3[NH:40][C:39]2=[O:48])[CH2:34][CH2:33]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:16][C:13]1[CH:12]=[CH:11][C:10]([C:7]2([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:8][CH2:9][CH:5]([N:32]3[CH2:33][CH2:34][CH:35]([N:38]4[C:42]5[CH:43]=[CH:44][C:45]([Cl:47])=[CH:46][C:41]=5[NH:40][C:39]4=[O:48])[CH2:36][CH2:37]3)[CH2:6]2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 13.5 g of 3,3-bis(p-fluorophenyl)cyclopentyl tosylate (nD20 1.5691), 7.5 g of 1-(4-piperidyl)-5-chloro-2-benzimidazolinone hydrochloride, 8.6 g of potassium carbonate and 70 ml of dimethylformamide is stirred at 70° C for 52 hours. The reaction mixture is poured into ice water, and the aqueous layer is removed by decantation. The precipitated semi-solid is dissolved in chloroform. The solution is washed with water and dried over sodium sulfate, and the solvent is removed. The crude crystals are recrystallized from a mixture of chloroform and ethanol (20:1) to give 1-[1-(3,3-bis(p-fluorophenyl)cyclopentyl)-4-piperidyl]-5-chloro-2-benzimidazolinone as white crystals, melting at 131°-134° C.

Workup

customthe aqueous layer is removed by decantation
dissolutionThe precipitated semi-solid is dissolved in chloroform
washThe solution is washed with water
dry with materialdried over sodium sulfate
customthe solvent is removed
customThe crude crystals are recrystallized from a mixture of chloroform and ethanol (20:1)

Sources & evidence

ORD record: ord-00fe439d9b8a46eab30fef0cc3505322
Source dataset: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04076821

Reaction notes

Loading…