1-(Morpholinocarbonylmethyl)piperazine → 4-Acetylmorpholine
Reaction equation
ClC1C=CC(C2C(C3C=CC(Cl)=CC=3)N(C(Cl)=O)C(C3C=CC(C(C)(C)COC)=CC=3OCC)=N2)=CC=1.[N:38]1([C:44](=[O:52])[CH2:45]N2CCNCC2)[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>>[N:38]1([C:44](=[O:52])[CH3:45])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1Participants
Procedure
4,5-Bis-(4-chloro-phenyl)-2-[2-ethoxy-4-(2-methoxy-1,1-dimethyl-ethyl)-phenyl]-4,5-dihydro-imidazole-1-carbonyl chloride (60 mg, 0.107 mmol) was reacted with 1-morpholin-4-yl-2-piperazin-1-yl-ethanone (34.2 mg, 0.161 mmol, Oakwood Products) using the procedure described in example 25 to give 4,5-bis-(4-chloro-phenyl)-2-[2-ethoxy-4-(2-methoxy-1,1-dimethyl-ethyl)-phenyl]-4,5-dihydro-imidazole-1-carbonyl}-piperazin-1-yl)-1-morpholin-4-yl-ethanone (70.1 mg) as white solids. The enantiomers were separated by chiral chromatography (Diacel ChiralPak OD, eluting with 40/60 hexane/ethanol). The first peak coming off the column is the desired 2-(4-{(4S,5R)-4,5-bis-(4-chloro-phenyl)-2-[2-ethoxy-4-(2-methoxy-1,1-dimethyl-ethyl)-phenyl]-4,5-dihydro-imidazole-1-carbonyl}-piperazin-1-yl)-1-morpholin-4-yl-ethanone (31.6 mg, white solids). HR-MS (ES, m/z): observed 736.3029, calculated for C39H48Cl2N5O5 [(M+H)+] 736.3027.
Sources & evidence
- ORD record
- ord-e13d70ade9a747588f02e7b9423a8a6d
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07964724B2
Reaction notes
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