HCID 22492878, compound → HCID 178468979, compound

HRID 1816326Notes

Reaction equation

HRID 1816326 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[H][H]>C(O)(C)(C)C.CO.[Ir]>[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:23][CH:24]=3)[CH2:12][CH2:13]2)[CH2:4][CH2:3]1.[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:23][CH:24]=3)[CH2:12][CH2:13]2)[CH2:4][CH2:3]1

Participants

7

Reactant 2

HCID 22492878HCID 22492878, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 178468979HCID 178468979, compoundHCID 178468980HCID 178468980, compound

Reagents, catalysts & solvents 3

HCID 23924IridiumCatalystHCID 887MethanolSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of ethyl 4-[4-(4-methylenecyclohexyl)-1-piperazinyl]benzoate (100 mg) and Iridium black (30 mg) in a mixture of t-butanol (1 ml) and methanol (2 ml) was stirred under atmospheric pressure of hydrogen for 4 hours. The catalyst was filtrated off and the filtrates were evaporated in vacuo. Ethyl 4-[cis-4-(4-methylcyclohexyl)-1-piperazinyl]benzoate and ethyl 4-[trans-4-(4-methylcyclohexyl)-1-piperazinyl]benzoate were obtained in the ratio 5:1-6:1 by thin-layer chromatography.

Workup

  1. filtrationThe catalyst was filtrated off
  2. customthe filtrates were evaporated in vacuo

Sources & evidence

ORD record
ord-b88d2bbe477d4ce1b15358487ad85f57
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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