Formaldehyde → 4-[(4-Dipropylaminobutyl)methylamino]methylbenzonitrile

HRID 1012564Notes

Reaction equation

HRID 1012564 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=O.[C:24]([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=1)[CH3:24])[CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 15965417HCID 15965417, compound

Product 1

HCID 161172934-[(4-Dipropylaminobutyl)methylamino]methylbenzonitrileYield 92%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

309 mg (1.07 mmol) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a) was added dropwise in a 100 ml recovery flask, and dissolved in 9.2 ml of anhydrous methanol. 0.134 ml of a formaldehyde aqueous solution (35%) was then added to the solution. 201.7 mg of sodium cyanoborohydride was then added to the mixture. After the addition of acetic acid to adjust the mixture to pH 5.0, the mixture was stirred at room temperature for 24 hours. 1 mol/l sodium hydroxide aqueous solution was then added to the mixture, followed by extraction with chloroform. The extract was dried over magnesium sulfate and concentrated, thereby obtaining 296.2 mg of 4-[(4-dipropylaminobutyl)methylamino]methylbenzonitrile (2b) was obtained as a colorless oily substance (yield: 92%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2c7f2ef4b50d4841958dbaf8921d9515
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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