Imidazole → 4-[4-(1H-imidazol-1-ylmethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone

HRID 2186145Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[C:14](=[O:32])[CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[NH:39]1[CH:43]=[CH:42][N:41]=[CH:40]1>CN(C=O)C>[N:39]1([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([S:9]([N:12]3[CH2:17][CH2:16][N:15]([CH2:18][CH:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)[C:14](=[O:32])[CH2:13]3)(=[O:11])=[O:10])=[CH:5][CH:4]=2)[CH:43]=[CH:42][N:41]=[CH:40]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-[4-(bromomethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone (430 mg), potassium carbonate (112 mg) and imidazole (83 mg) in DMF (15 ml) was stirred at 70° C. for 1 hour. The reaction solution was concentrated, and to the residue was added water. The mixture was extracted with ethyl acetate, washed with water, sodium bicarbonate solution and brine, dried and concentrated, and the residue was recrystallized from ethyl acetate/hexane to give colorless crystals of 4-[4-(1H-imidazol-1-ylmethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone (421 mg).

Workup

concentrationThe reaction solution was concentrated
additionto the residue was added water
extractionThe mixture was extracted with ethyl acetate
washwashed with water, sodium bicarbonate solution and brine
customdried
concentrationconcentrated
customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-6a155bb5a56842c4bac152450eaf5d98
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403595B1

Reaction notes

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