Acetic Anhydride → Acetamide, N-[(1S)-1-(1-naphthalenyl)ethyl]-

HRID 1762068Notes

Reaction equation

[C:1]1([C@@H:11]([NH2:13])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:14]([NH:13][C@H:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:12])(=[O:16])[CH3:15]

Participants

Conditions

Temperature: 38 °C

Procedure

5 g of (S)-(-)-α-(1-naphthyl)ethylamine (manufactured by Hydras Kagaku) was dissolved in 20 ml of pyridine, and 5.07 mg of acetic anhydride was added thereto under cooling with ice. The mixture was stirred at 38° C. for 12 hours. The reaction solution was diluted with 500 ml of chloroform, and the organic layer was sequentially washed with a dilute hydrochloric acid aqueous solution, a dilute sodium hydroxide aqueous solution and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The reaction mixture thus obtained was recrystallized from dried ethanol to obtain 6.3 g of N-acetyl-(S)-α-(1-naphthyl)ethylamine. This substance is a known compound, and the measured values of various physical properties agreed to the values disclosed in literatures.

Workup

temperatureunder cooling with ice
washthe organic layer was sequentially washed with a dilute hydrochloric acid aqueous solution
dry with materiala dilute sodium hydroxide aqueous solution and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customThe reaction mixture thus obtained
customwas recrystallized from dried ethanol

Sources & evidence

ORD record: ord-83bb455b62c44d889418db4af67ac3f6
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04830921

Reaction notes

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