Acetic Anhydride → 2-Phenylazepane-1-carbaldehyde
Reaction equation
C(O[C:5](=[O:7])C)(=O)C.[C:8]1([CH:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)=O>[CH:5]([N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:14]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a mixture of, 98-100% formic acid (30 ml) and acetic anhydride (100 ml) was added 2-(R,S)-phenylazacycloheptane (10 g, 57.1 mmol; B. E. Maryanoff et al., J.Med. Chem., 30, 1433, 1987) and the mixture warmed to 70° C. for 2 h. The reaction mixture was then cooled and evaporated to dryness in vacuo and the residue was partitioned between ether and saturated aqueous potassium carbonate. The ether layer was separated and evaporated to dryness in vacuo to afford the title compound (11.24 g; 97%) as a mixture of E/Z isomers.