Sodium Hydroxide → HCID 15965417, compound

HRID 1012563Notes

Reaction equation

HRID 1012563 reaction equation
Cl.[CH2:2]([N:5]([CH2:20][CH2:21][CH3:22])[CH2:6][CH2:7][CH2:8][CH2:9][NH:10][CH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[CH2:3][CH3:4].[OH-].[Na+]>O>[CH2:20]([N:5]([CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7][CH2:8][CH2:9][NH:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]#[N:17])=[CH:18][CH:19]=1)[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67314471HCID 67314471, compound

Product 1

HCID 15965417HCID 15965417, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After dissolving 9.07 g of the resulting hydrochloride (2aa) in 50 ml of water (pH=6.0), the mixture was neutralized with a 25% sodium hydroxide aqueous solution (pH=9.0 to 10.0), followed by extraction with 100 ml of chloroform twice. The chloroform layer was washed with 50 ml of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated, thereby obtaining 6.9 g of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a) as a colorless oily substance (yield: 97%, GC: 99.4%).

Workup

  1. extractionfollowed by extraction with 100 ml of chloroform twice
  2. washThe chloroform layer was washed with 50 ml of a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab326b939efd4baab687d8e4165df922
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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