1-(3-Cyanopropyl)piperazine → N-[3-(10,11-dihydro-dibenzo[b,f]azepine-5-yl)-propyl]-N'-(3-cyanopropyl)-piperazine
Reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]([CH2:16][CH2:17][CH:18]=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:20]([CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)#[N:21]>C(Cl)Cl>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]([CH2:16][CH2:17][CH2:18][N:28]3[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][CH2:22][C:20]#[N:21])[CH2:26][CH2:27]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Na(Oac)3BH3 (171 mg, 0.80 mmol) were added to a solution of 3-(10,11-dihydro-dibenzo[b,f]azepine-5-yl)-propionaldehyde (100 mg, 0.40 mmol) and N-(3-cyanopropyl)-piperazine (122 mg, 0.80 mmol) in CH2Cl2 (10 ml). After 16 hours of stirring, the mixture was diluted with CH2Cl2 (50 ml) and washed with a saturated solution of NaHCO3. The organic phase was dried (Na2SO4) and evaporated. Purification using flash chromatography of the residue obtained yielded N-[3-(10,11-dihydro-dibenzo[b,f]azepine-5-yl)-propyl]-N′-(3-cyanopropyl)-piperazine (yield: 106 mg, 68%).