Hydrochloric Acid → 4-acetyl-N-[2-(2-naphthalenyloxy)ethyl]benzamide

HRID 2225768Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][NH2:14].[C:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1)(=[O:17])[CH3:16].Cl>ClCCl.C(N(CC)CC)C.O>[C:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:14][CH2:13][CH2:12][O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[O:23])=[CH:20][CH:19]=1)(=[O:17])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred mixture of 2-(2-naphthalenyloxy)ethanamine (4.9 g) in dichloromethane (25 mL) and triethylamine (5 mL) was chilled to 0° C. and treated with the acid chloride prepared from 4-acetyl benzoic acid (4.3 g) and then the mixture was stirred at room temperature for 10 minutes. The mixture was diluted with water and acidified with excess 2N hydrochloric acid, extracted with dichloromethane and the organic layer was washed in turn with sodium bicarbonate solution and saturated sodium chloride solution. The organic layer was dried (Na2SO4), filtered, and evaporated to give crude material which was purified by HPLC (ethyl acetate-dichloromethane; 1:9) and crystallized from ethyl acetate to provide 4.7 g of 4-acetyl-N-[2-(2-naphthalenyloxy)ethyl]benzamide as a colorless solid, mp 131°-132° C.

Workup

extractionextracted with dichloromethane
washthe organic layer was washed in turn with sodium bicarbonate solution and saturated sodium chloride solution
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
customevaporated
customto give crude material which
customwas purified by HPLC (ethyl acetate-dichloromethane; 1:9)
customcrystallized from ethyl acetate

Sources & evidence

ORD record: ord-13b83de00b124d27b5d522e2a7d143b0
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344843

Reaction notes

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