Triethylamine → N-(2-methylcyclopentyl)-3,5-dimethoxy-4-(2-propynyloxy)benzamide

HRID 601999Notes

Reaction equation

HRID 601999 reaction equation
Cl.[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[NH2:8].C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([O:31][CH3:32])[C:26]=1[O:27][CH2:28][C:29]#[CH:30])[C:21](Cl)=[O:22]>C(OCC)(=O)C>[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[NH:8][C:21](=[O:22])[C:20]1[CH:19]=[C:18]([O:17][CH3:16])[C:26]([O:27][CH2:28][C:29]#[CH:30])=[C:25]([O:31][CH3:32])[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 191014392-Methylcyclopentan-1-amine hydrochlorideHCID 574456693,5-Dimethoxy-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57701153N-(2-methylcyclopentyl)-3,5-dimethoxy-4-(2-propynyloxy)benzamideYield 67.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 1 ml of ethyl acetate and 0.2 g of 2-methylcyclopentylamine hydrochloride was added 0.48 ml of triethylamine and then, a mixture of 0.25 g of 3,5-dimethoxy-4-(2-propynyloxy)benzoyl chloride and 1 ml of ethyl acetate was added dropwise thereto under ice cooling. The mixture obtained was stirred at room temperature for 12 hours. Then, the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.21 g of N-(2-methylcyclopentyl)-3,5-dimethoxy-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 68 of the present invention) represented by the formula:

Workup

  1. additionwas added dropwise
  2. customThe mixture obtained
  3. concentrationThen, the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2c8844ad818a46f1947c88d603eaaa41
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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