4-Chlorobenzylamine → 252956-41-5

HRID 1836704Notes

Reaction equation

HRID 1836704 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[C:10]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)#[N:11].[BH3-]C#N.[Na+]>C(=O)(O)[O-].[Na+].[Cl-].[Cl-].[Zn+2]>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][CH2:16][C:15]2[CH:18]=[CH:19][C:12]([C:10]#[N:11])=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 660364-ChlorobenzylamineHCID 660424-CyanobenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 1091740252956-41-5

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

To a methanolic solution (20 mL) of 4-chlorobenzylamine (1.02 g, 7.2 mmol) was added successively ZnCl2 (0.981 g, 7.2 mmol), 4-cyanobenzaldehyde (1.007 g, 7.3 mmol), and NaCNBH3 (0.452 g, 7.2 mmol). The reaction mixture was stirred at r.t. for 2 days. It was diluted with aq. sodium bicarbonate and the reaction mixture was extracted with methylene chloride. The combined organic extracts were washed with brine, dried over magnesium sulfate and concentrated. The product (compound 22) was purified by silica gel chromatography: 1.43 g (77%).

Workup

  1. extractionthe reaction mixture was extracted with methylene chloride
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe product (compound 22) was purified by silica gel chromatography

Sources & evidence

ORD record
ord-01746bf5f0244d9ab75335fc2b2c9491
Source dataset
uspto-grants-2004_08
Patent number
US06777561B1

Reaction notes

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