Methyl 4-(chlorocarbonyl)benzoate → (+/-)-cis-n-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-4-methoxycarbonylbenzamide

HRID 635825Notes

Reaction equation

HRID 635825 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].[CH3:18][O:19][C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)=[O:21]>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:26](=[O:27])[C:25]2[CH:24]=[CH:23][C:22]([C:20]([O:19][CH3:18])=[O:21])=[CH:30][CH:29]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 14321190(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene

Product 1

HCID 53911096(+/-)-cis-n-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-4-methoxycarbonylbenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

2.6 g of (+/−)-cis-1,2-dimethoxy-4-(2-aminocyclohexyl)benzene are dissolved in 20 ml of methylene chloride and 1 ml of triethylamine. At RT, a solution of 2.4 g of 4-methoxycarbonylbenzoyl chloride in 30 ml of methylene chloride is added dropwise over a period of 3 h, and the mixture is stirred for 1 h and then extracted with 50 ml each of water, 2 N hydrochloric acid, sat. sodium bicarbonate solution and once more with water. The organic phase is dried with sodium sulfate, concentrated and crystallized from ethyl acetate. This gives 2.0 g (45.5% of Th.) of the title compound of m.p. 139-143° C.

Workup

  1. extractionextracted with 50 ml each of water, 2 N hydrochloric acid, sat. sodium bicarbonate solution and once more with water
  2. dry with materialThe organic phase is dried with sodium sulfate
  3. concentrationconcentrated
  4. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0f4d67a2a10c42c4a0c21f179ac7cc0a
Source dataset
uspto-grants-2001_02
Patent number
US06191138B1

Reaction notes

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