Hydrochloric Acid → N-(4-Dimethylamino-4-phenylcyclohexyl)-4-phenoxybutyramide hydrochloride
Reaction equation
CN(C)C1(C2C=CC=CC=2)CCC(N)CC1.O(CCCC([Cl:29])=O)C1C=CC=CC=1.[CH3:30][N:31]([CH3:57])[C:32]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:37][CH2:36][CH:35]([NH:38][C:39](=[O:50])[CH2:40][CH2:41][CH2:42][O:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:34][CH2:33]1.Cl.Cl[Si](C)(C)C>CC(=O)CC.C(OCC)(=O)C.O.C(OCC)C.CO.C(OCC)C>[ClH:29].[CH3:57][N:31]([CH3:30])[C:32]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:33][CH2:34][CH:35]([NH:38][C:39](=[O:50])[CH2:40][CH2:41][CH2:42][O:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:36][CH2:37]1Participants
11
Reactant 5
Product 1
Reagents, catalysts & solvents 5
Procedure
As described for Example 235, a cis/trans mixture of N,N-dimethyl-1-phenylcyclohexane-1,4-diamine (800 mg) was reacted with 0.95 mg 4-phenoxybutyryl chloride and the crude product (1.48 g) was isolated analogously. By chromatography on silica gel (3.0×19 cm) with 100 ml diethyl ether followed by 400 ml diethyl ether/methanol (v:v=2:1), 450 mg of the more polar diastereoisomer of N-(4-dimethylamino-4-phenylcyclohexyl)-4-phenoxybutyramide were obtained and, as a solution in 5 ml 2-butanone and 5 ml ethyl acetate, were converted into the corresponding hydrochloride by addition of 21.3 μl water and 150 μl chlorotrimethylsilane (420 mg of a white solid, m.p. 191-192° C.).
Workup
- customthe crude product (1.48 g) was isolated analogously
Sources & evidence
- ORD record
- ord-50f486e8e9d34d65afe5359b6ef57bce
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786328B2
Reaction notes
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