4-Bromobenzaldehyde → HCID 16117294, compound

HRID 1012577Notes

Reaction equation

HRID 1012577 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].[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][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:25][CH:24]=1

Participants

6

Reactant 4

HCID 707414-BromobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15965417HCID 15965417, compound

Product 1

HCID 16117294HCID 16117294, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

0.40 g (1.39 mmol) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a), 8.0 ml of ethanol, and 514 mg (2.78 mmol, 2.0 equivalents) of 4-bromobenzaldehyde were charged in a 50 ml recovery flask under a nitrogen stream. The mixture was then cooled to 0° C. After the addition of 0.707 g (3.34 mmol, 2.4 equivalents) of sodium triacetoxyborohydride, the mixture was stirred for 22 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 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 (manufactured by FujiSilysia Chemical Ltd.), n-hexane:ethyl acetate=3:1), thereby obtaining 0.508 g of 4-{[(4-bromobenzyl)-(4-dipropylaminobutyl)amino]methyl}benzonitrile (15) as a light yellow oily substance (yield: 80.0%). [HPLC: 96.2% (HPLC measurement conditions B)]

Workup

  1. extractionextracted 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 (manufactured by FujiSilysia Chemical Ltd.), n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f977fe25294642c69de006d191092184
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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