Acetic Acid → 3,5-Dibenzyl-2-(piperazin-1-yl)-3,5-dihydro-imidazo[4,5-c]pyridin-4-one

HRID 2214446Notes

Reaction equation

C(O)(=O)C.[NH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[CH2:11]([N:18]1[C:22]2[C:23](=[O:34])[N:24]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1S(C)(=O)=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N>O>[CH2:11]([N:18]1[C:22]2[C:23](=[O:34])[N:24]([CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 150 °C

Procedure

660 mg (11 mmol) of glacial acetic acid were added dropwise to 860 mg (10 mmol) of piperazine with cooling, then 180 mg of 3,5-dibenzyl-2-methanesulphonyl-3,5-dihydro-imidazo[4,5-c]pyridin-4-one (crude product from Example 3 h) were added and the mixture was stirred for 24 hours at 150° C. After cooling approx. 10 ml of water were added, the mixture was made alkaline with concentrated ammonia solution and the mixture was extracted three times with 5 ml of dichloromethane. The extracts were dried over sodium sulphate and concentrated by evaporation. The crude product thus obtained was purified by column chromatography (silica gel; eluant:petroleum ether with 20–60% ethyl acetate).

Workup

temperaturewith cooling
additionwere added
extractionthe mixture was extracted three times with 5 ml of dichloromethane
dry with materialThe extracts were dried over sodium sulphate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-ca3933c2e6dc442492101b65fb3b194d
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109192B2

Reaction notes

Loading…