Tetrahydrofuran → N-cyclohexylmethyl-4-(2-propynyloxy)-3-methoxybenzamide

HRID 601982

Reaction equation

HRID 601982 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]#[CH:20])[C:11](Cl)=[O:12].[CH:21]1([CH2:27][NH2:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C(N(CC)CC)C>[CH:21]1([CH2:27][NH:28][C:11](=[O:12])[C:10]2[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]#[CH:20])=[C:8]([O:7][CH3:6])[CH:9]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 76688CyclohexanemethylamineHCID 574456713-Methoxy-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57445682N-cyclohexylmethyl-4-(2-propynyloxy)-3-methoxybenzamideYield 82%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 10 ml of THF and 0.20 g of 3-methoxy-4-(2-propynyloxy)benzoyl chloride were added dropwise 0.22 g of cyclohexylmethylamine and 0.20 g of triethylamine in order under ice cooling The mixture obtained was stirred at room temperature for 4 hours. Then, the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.22 g of N-cyclohexylmethyl-4-(2-propynyloxy)-3-methoxybenzamide (hereinafter, described as the compound 17 of the present invention) represented by the formula:

Workup

  1. customobtained
  2. concentrationThen, the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9cd950a9440c48c49d51b3c206f62b4d
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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