1,3-Benzodioxole-5-carbonyl chloride → (-)-cis-n-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-3,4-methylenedioxybenzamide

HRID 1017618Notes

Reaction equation

HRID 1017618 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].[CH2:18]1[O:29][C:28]2[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][C:20]=2[O:19]1>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:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:28]3[O:29][CH2:18][O:19][C:20]=3[CH:21]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 14321190(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene2×

Product 1

HCID 54164802(-)-cis-n-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-3,4-methylenedioxybenzamideYield 95.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

4.0 g of (−)-cis-1,2-dimethoxy-4-(2-aminocyclohexyl)benzene (compound B2) are dissolved in 100 ml of methylene chloride and 5.0 ml of triethylamine. A solution of 3.8 g of 3,4-methylenedioxybenzoyl chloride in 50 ml of methylene chloride is added dropwise at RT and the mixture is extracted with 100 ml each of water, 2N hydrochloric acid, satd. sodium hydrogencarbonate solution and water again after stirring overnight. The organic phase is dried using sodium sulfate and concentrated. 6.2 g of the title compound are obtained.

Workup

  1. extractionthe mixture is extracted with 100 ml each of water, 2N hydrochloric acid
  2. customThe organic phase is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e7f4af18d6804e93a2cc60f50f52e9c6
Source dataset
uspto-grants-2002_11
Patent number
US06479505B1

Reaction notes

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