1-(3-Cyanopropyl)piperazine → N-[3-(10,11-dihydro-dibenzo[b,f]azepine-5-yl)-propyl]-N'-(3-cyanopropyl)-piperazine

HRID 552065Notes

Reaction equation

HRID 552065 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]=1

Participants

4

Reactant 2

HCID 27579771-(3-Cyanopropyl)piperazineHCID 866302043-(10,11-Dihydro-dibenzo[b,f]azepine-5-yl)-propionaldehyde

Product 1

HCID 67164489N-[3-(10,11-dihydro-dibenzo[b,f]azepine-5-yl)-propyl]-N'-(3-cyanopropyl)-piperazineYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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%).

Workup

  1. washwashed with a saturated solution of NaHCO3
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated
  4. customPurification
  5. customobtained

Sources & evidence

ORD record
ord-728d128765b14fd190e68e930061de75
Source dataset
uspto-grants-2011_05
Patent number
US07951796B2

Reaction notes

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