Triethylamine → N-cyclohexylmethyl-4-(2-propynyloxy)-3,5-dimethoxybenzamide

HRID 601979Notes

Reaction equation

HRID 601979 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:16]([O:19][C:20]1[C:28]([O:29][CH3:30])=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][C:21]=1[O:31][CH3:32])[C:17]#[CH:18]>C(OCC)(=O)C>[CH:1]1([CH2:7][NH:8][C:24](=[O:25])[C:23]2[CH:22]=[C:21]([O:31][CH3:32])[C:20]([O:19][CH2:16][C:17]#[CH:18])=[C:28]([O:29][CH3:30])[CH:27]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 574456693,5-Dimethoxy-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57445670N-cyclohexylmethyl-4-(2-propynyloxy)-3,5-dimethoxybenzamideYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

A mixture of 3.6 g of cyclohexylmethylamine, 3.5 g of triethylamine and 10 ml of ethyl acetate was added dropwise under ice cooling to a mixture of 75 ml of ethyl acetate and 7.4 g of 4-(2-propynyloxy)-3,5-dimethoxybenzoyl chloride. The mixture obtained was stirred at room temperature for 4 hours. Then, ethyl acetate was added to the reaction mixture and it was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 7.7 g of N-cyclohexylmethyl-4-(2-propynyloxy)-3,5-dimethoxybenzamide (hereinafter, described as the compound 1 of the present invention) represented by the formula:

Workup

  1. customThe mixture obtained
  2. filtrationwas filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2a391536e7104a91b7ced54197694bda
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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