(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene → (-)-cis-n-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-4-benzoylbenzamide

HRID 1016277Notes

Reaction equation

HRID 1016277 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[NH2:15])=[CH:5][C:4]=1[O:16][CH3:17].CO[C:20]1[CH:25]=[C:24](O)[C:23]([C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:28])=[CH:22][C:21]=1S(O)(=O)=O.[C:39](Cl)(Cl)=[O:40]>C(Cl)Cl.C(N(CC)CC)C>[CH3:17][O:16][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:39](=[O:40])[C:20]2[CH:21]=[CH:22][C:23]([C:27](=[O:28])[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:24][CH:25]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 14321190(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene2×HCID 131723626Benzophenone-4 carbonyl chloride

Product 1

HCID 53821352(-)-cis-n-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-4-benzoylbenzamideYield 145.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

4.0 g of (−)-cis-1,2-dimethoxy-4-(2-aminocyclohexyl)-benzene (compound B4) are dissolved in 40 ml of methylene chloride and 10.0 ml of triethylamine. A solution of 4.9 g of benzophenone-4-carbonyl chloride in 100 ml of methylene chloride is added dropwise at RT and the mixture is extracted, after stirring overnight, with 50 ml each of water, 2N hydrochloric acid, satd sodium hydrogencarbonate solution and water again. The organic phase is dried using sodium sulfate and concentrated. 7.78 g of the title compound are obtained as a crystallizing oil. M.p. 119-122.5° C.

Workup

  1. extractionthe mixture is extracted
  2. customThe organic phase is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5048f271929746e8ae2a9e0545d952dc
Source dataset
uspto-grants-2002_11
Patent number
US06476025B1

Reaction notes

Loading…