HCID 19380545, compound → HCID 178513639, compound

HRID 2050431Notes

Reaction equation

HRID 2050431 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH:7]=[C:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1>[Pt].C.O1CCOCC1.C(N(CC)CC)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[CH:21][CH:22]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 19380545HCID 19380545, compound

Product 1

HCID 178513639HCID 178513639, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 16218561HCID 16218561, compoundCatalystHCID 68453242Dioxan triethylamineSolvent

Procedure

A mixture of 500 mg of 4-[4-[2-(1,3-dioxolan-2-yl)ethylidene]cyclohexyl]benzamide and 20 ml of dioxan/triethylamine (vol. 9:1) was hydrogenated in the presence of 500 mg of 10 percent platinum-charcoal for 2 hours. The reaction mixture was then filtered and the filtrate was evaporated. Recrystallization of the evaporation residue from 40 ml of dioxan gave 230 mg of 4-[trans-4-[2-(1,3-dioxolan-2-yl)ethyl]cyclohexyl]benzamide as colorless crystals.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customthe filtrate was evaporated
  3. customRecrystallization of the evaporation residue from 40 ml of dioxan

Sources & evidence

ORD record
ord-f990f42e8bff4699a1bc38b023b90f57
Source dataset
uspto-grants-1991_05
Patent number
US05013477

Reaction notes

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