4-(Diethylamino)benzaldehyde → HCID 16117295, compound

HRID 1012578Notes

Reaction equation

HRID 1012578 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].[CH2:22]([N:24]([CH2:33][CH3:34])[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)[CH3:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:33]([N:24]([CH2:22][CH3:23])[C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=2)[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:19][CH2:20][CH3:21])=[CH:27][CH:26]=1)[CH3:34]

Participants

6

Reactant 4

HCID 671144-(Diethylamino)benzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15965417HCID 15965417, compound

Product 1

HCID 16117295HCID 16117295, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

0.473 g (1.65 mmol) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a), 9.5 ml of ethanol, and 583 mg (3.29 mmol, 2.0 equivalents) of 4-diethylaminobenzaldehyde were charged in a 50 ml recovery flask under a nitrogen stream. The mixture was then cooled to 0° C. After the addition of 0.837 g (3.95 mmol, 2.4 equivalents) of sodium triacetoxyborohydride, the mixture was stirred at room temperature for 17 hours. After confirming the disappearance of the raw material by TLC, the reaction solution was added to 50 ml of a saturated sodium bicarbonate aqueous solution, and was extracted twice with 50 ml of chloroform. The chloroform layer was washed with 100 ml of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, concentrated, and purified by silica gel column chromatography (Chromatorex NH, chloroform:n-hexane=1:1), thereby obtaining 0.252 g of 4-{[(4-diethylaminobenzyl)-(4-dipropylaminobutyl)amino]methyl}benzonitrile (16) as a light yellow oily substance (yield: 34.1%). [HPLC: 98.7% (HPLC measurement conditions B)]

Workup

  1. extractionwas extracted twice with 50 ml of chloroform
  2. washThe chloroform layer was washed with 100 ml of a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (Chromatorex NH, chloroform:n-hexane=1:1)

Sources & evidence

ORD record
ord-cf5dd77c7d744fad828c16420961c869
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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