Hydrochloric Acid → 5-Methyl-3-phenylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide hydrochloride

HRID 418317Notes

Reaction equation

HRID 418317 reaction equation
CN(C)C1(C2C=CC=CC=2)CCC(N)CC1.CC1ON=C(C2C=CC=CC=2)C=1C(O)=O.Cl.[CH3:33][N:34]([CH3:62])[C:35]1([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH2:40][CH2:39][CH:38]([NH:41][C:42]([C:44]2[C:45]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[N:46][O:47][C:48]=2[CH3:49])=[O:43])[CH2:37][CH2:36]1.[Cl:63][Si](C)(C)C>CC(=O)CC.O.C(OCC)(=O)C.C(OCC)C.CO.C(OCC)C>[ClH:63].[CH3:62][N:34]([CH3:33])[C:35]1([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH2:40][CH2:39][CH:38]([NH:41][C:42]([C:44]2[C:45]([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)=[N:46][O:47][C:48]=2[CH3:49])=[O:43])[CH2:37][CH2:36]1

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 129862564-Dimethylamino-4-phenyl-cyclohexylamineHCID 666514015-Methyl-3-phenylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide

Product 1

HCID 666518365-Methyl-3-phenylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide hydrochloride

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

As described for Example 120, 650 mg of a cis-trans mixture of N,N-dimethyl-1-phenylcyclohexane-1,4-diamine were reacted with 600 mg 5-methyl-3-phenylisoxazole-4-carboxylic acid (1 molar equivalent) and the crude product was isolated. The main fraction, obtained after column chromatography on silica gel (3.0×18 cm) with 100 ml diethyl ether followed by 350 ml diethyl ether/methanol (V:V=2:1), of 560 mg was dissolved in 20 ml 2-butanone and 10 ml ethyl acetate and converted into the corresponding hydrochloride of the non-polar diastereoisomer of 5-methyl-3-phenylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide by adding 25 μl water and 176 μl chlorotrimethylsilane (372 mg of white solid, Mp. 220-224° C.).

Workup

  1. customthe crude product was isolated

Sources & evidence

ORD record
ord-3454abac947f4cd48f1f3b516222f14e
Source dataset
uspto-grants-2012_01
Patent number
US08093272B2

Reaction notes

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