Triethylamine → 4-(2-Bromo-5-fluorophenoxy)piperidine-1-carbonitrile
Reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[N:16]#[C:17]Br.C(N(CC)CC)C>C1COCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:17]#[N:16])[CH2:9][CH2:10]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(2-bromo-5-fluorophenoxy)piperidine (2.0 g, 7.30 mmol) in THF (24.3 ml) was added cyanogen bromide (0.77 g, 7.30 mmol) followed by triethylamine (1.01 ml, 7.3 mmol) at 0° C. The mixture was warmed to rt and further stirred for 1 h. Solvent was evaporated and the residue was diluted with 1N HCl (20 mL). The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic fractions were washed with water (20 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure to afford the title compound as a solid which was used in the next step without further purification.