Acetic Anhydride → N-acetyl-N-[3-(3-methoxyphenyl)cyclohexyl]amine

HRID 1108762Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C@H:16]2[CH2:21][CH2:20][CH2:19][C@H:18]([NH2:22])[CH2:17]2)[CH:13]=[CH:14][CH:15]=1.O.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:1]([NH:22][CH:18]1[CH2:19][CH2:20][CH2:21][CH:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH3:8])[CH:11]=2)[CH2:17]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

Acetic anhydride (1 ml) and pyridine (0.5 ml) were added to (trans)-3-(3-methoxyphenyl) cyclohexylamine (10 mg) and the mixture was stirred at 50° C. for 2 hours. The reaction solution was poured into glacial sodium bicarbonate water and extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid, saturated sodium bicarbonate water and saturated saline and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to give 8 mg of N-acetyl-N-[3-(3-methoxyphenyl)cyclohexyl]amine (53.3%).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with 1 N hydrochloric acid, saturated sodium bicarbonate water and saturated saline
dry with materialdried with anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-cb3aa7060fca4e96a479139be1154639
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069176

Reaction notes

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