Water → (R)-3-acetyl-1-[1-(acenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzoimidazol-2-one

HRID 230464Notes

Reaction equation

[C@H:1]1([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[NH:21][C:20]3=[O:28])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[H-].[Na+].[C:31](Cl)(=[O:33])[CH3:32].O>CN(C=O)C>[C:31]([N:21]1[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:19]([CH:16]2[CH2:17][CH2:18][N:13]([C@H:1]3[C:11]4=[C:12]5[C:7](=[CH:8][CH:9]=[CH:10]4)[CH:6]=[CH:5][CH:4]=[C:3]5[CH2:2]3)[CH2:14][CH2:15]2)[C:20]1=[O:28])(=[O:33])[CH3:32]

Participants

Conditions

Temperature: 50 °C

Procedure

(R)-1-[1-(Acenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzoimidazol-2-one (6.2 g, 16.8 mmol) was dissolved in DMF (60 ml). Sodium hydride (0.9 g, 60%) was added and the suspension was stirred at 50° C. for 30 min. It was cooled to room temperature and acetyl chloride (1.5 g, 19 mmol) was added and the mixture was stirred for 3 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated aqueous ammonium chloride solution, dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (6.3 g) as pale-yellow crystals

Workup

temperatureIt was cooled to room temperature
stirringthe mixture was stirred for 3 hr
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated aqueous ammonium chloride solution
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record: ord-9fb6721f66cf43f6b7962aa60e0f84f4
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566728B2

Reaction notes

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