Hydrochloric Acid → N-(4-Dimethylamino-4-phenylcyclohexyl)-4-phenoxybutyramide hydrochloride

HRID 507878Notes

Reaction equation

HRID 507878 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:7][CH:6]([NH:9][C:10](=[O:21])[CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:5][CH2:4]1.Cl.O.[Cl:31][Si](C)(C)C>CC(=O)CC.C(OCC)(=O)C>[ClH:31].[CH3:28][N:2]([CH3:1])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:4][CH2:5][CH:6]([NH:9][C:10](=[O:21])[CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 11546187N-(4-dimethylamino-4-phenylcyclohexyl)-4-phenoxybutyramide

Product 1

HCID 11546186N-(4-Dimethylamino-4-phenylcyclohexyl)-4-phenoxybutyramide hydrochloride

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

As described for Example 237, 575 mg of the less polar diastereoisomer of N-(4-dimethylamino-4-phenylcyclohexyl)-4-phenoxybutyramide were also obtained and, as a solution in 5 ml 2-butanone and 5 ml ethyl acetate, were converted into the corresponding hydrochloride by addition of 27.2 μl water and 190 μl chlorotrimethylsilane (530 mg of a white solid, m.p. 194-197° C.).

Sources & evidence

ORD record
ord-70e615d71e504a42a9ea129c3a638a2f
Source dataset
uspto-grants-2010_08
Patent number
US07786328B2

Reaction notes

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