Methanol → (-)-cis-N-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-4-propionylbenzamide

HRID 1016280Notes

Reaction equation

HRID 1016280 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[N+:15]([O-])=O)=[CH:5][C:4]=1[O:18][CH3:19].[OH2:20].NN.[CH3:23][OH:24]>[Ni]>[CH3:19][O:18][C:4]1[CH:5]=[C:6]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[NH:15][C:23](=[O:24])[C:3]2[CH:8]=[CH:7][C:6]([C:9](=[O:20])[CH2:10][CH3:11])=[CH:5][CH:4]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 15389590(+/-)-cis1,2-Dimethoxy-4-(2-nitrocyclohexyl)benzene

Product 1

HCID 53868529(-)-cis-N-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-4-propionylbenzamide

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

8.5 g of (+/−)-cis-1,2-dimethoxy-4-(2-nitrocyclohexyl)benzene are dissolved in 400 ml of methanol and treated at RT with 7 ml of hydrazine hydrate and 2.5 g of Raney nickel in portions in the course of 8 h. After stirring overnight at RT, the reaction mixture is filtered, the filtrate is concentrated and the residue is chromatographed on silica gel using a mixture of toluene/ethyl acetate/triethylamine=4/2/0.5. The title compound is obtained as an oil.

Workup

  1. filtrationthe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customthe residue is chromatographed on silica gel using
  4. additiona mixture of toluene/ethyl acetate/triethylamine=4/2/0.5

Sources & evidence

ORD record
ord-df0caf3b1288468981385b5f6c071991
Source dataset
uspto-grants-2002_11
Patent number
US06476025B1

Reaction notes

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