4-Cyanobenzaldehyde → HCID 67315062, compound

HRID 1012567Notes

Reaction equation

HRID 1012567 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[CH2:2][CH3:3].[C:22]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)#[N:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:28][C:27]1[CH:30]=[CH:31][C:24]([C:22]#[N:23])=[CH:25][CH:26]=1)[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=1)[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 660424-CyanobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15965417HCID 15965417, compound

Product 1

HCID 67315062HCID 67315062, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-30 °C

Procedure

1.0 g (3.47 mmol, 1.0 equivalent) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a), 10 ml of ethanol, and 684 mg (5.21 mmol, 1.5 equivalents) of 4-cyanobenzaldehyde were charged in a 100 ml three-necked flask. The mixture was cooled to −30° C. After the addition of 1.47 g (6.95 mmol, 2.0 equivalents) of sodium triacetoxyborohydride, the mixture was stirred for six hours and further stirred at room temperature for 12 hours. After confirming the disappearance of the raw material, the reaction solution was added into 50 ml of a saturated sodium bicarbonate aqueous solution, and extracted with 100 ml of chloroform. The chloroform layer was washed with 50 ml of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated, thereby obtaining 1.35 g of 4-[(4-dipropylaminobutyl)-4-cyanobenzylamino]methylbenzonitrile (12) as a colorless oily substance (yield: 97%, GC: 87%).

Workup

  1. stirringfurther stirred at room temperature for 12 hours
  2. extractionextracted with 100 ml of chloroform
  3. washThe chloroform layer was washed with 50 ml of a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4d65642d303043d9bb8e1935972afe5f
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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