3,4-Bis(cyclopropylmethoxy)benzoyl chloride → (+/-)-cis-3,4-bis-cyclopropylmethoxy-N-[6-(3,4-dimethoxyphenyl)cyclohex-3-enyl]benzamide

HRID 220105Notes

Reaction equation

HRID 220105 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:11]2[C@H:16]([NH2:17])[CH2:15][CH:14]=[CH:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH:18]1([CH2:21][O:22][C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=2[O:32][CH2:33][CH:34]2[CH2:36][CH2:35]2)[C:26](Cl)=[O:27])[CH2:20][CH2:19]1>ClCCl>[CH:18]1([CH2:21][O:22][C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=2[O:32][CH2:33][CH:34]2[CH2:36][CH2:35]2)[C:26]([NH:17][C@H:16]2[C@@H:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:12][CH:13]=[CH:14][CH2:15]2)=[O:27])[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 179890793,4-Bis(cyclopropylmethoxy)benzoyl chlorideHCID 86601281(+/-)-cis-6-(3,4-Dimethoxyphenyl)-cyclohex-3-enylamine

Product 1

HCID 86601280(+/-)-cis-3,4-bis-cyclopropylmethoxy-N-[6-(3,4-dimethoxyphenyl)cyclohex-3-enyl]benzamideYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

20 g of (±)-cis-6-(3,4-dimethoxyphenyl)-cyclohex-3-enylamine (compound G1) are dissolved in 125 ml of dichloromethane and treated with a solution of 24.1 g of 3,4-bis-cyclopropylmethoxybenzoyl chloride in 125 ml of dichloromethane at room temperature. After 1 h the reaction mixture is extracted with 2 N hydrochloric acid and water, the organic phase is dried using sodium sulfate and concentrated. 38.3 g of the title compound of m.p. 152-153.5° C. are obtained.

Workup

  1. extractionAfter 1 h the reaction mixture is extracted with 2 N hydrochloric acid and water
  2. customthe organic phase is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-797f5f09450d48fe84deae6d1faf378e
Source dataset
uspto-grants-2012_06
Patent number
US08202880B2

Reaction notes

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