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

HRID 1840557Notes

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-99bd46b161df432ea3d659eec3f7d6f7
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680312B2

Reaction notes

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