Acetyl chloride → HCID 12839032, compound

HRID 230626Notes

Reaction equation

HRID 230626 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[Br:12][C:13]1[CH:21]=[CH:20][C:16]([CH2:17][NH:18][CH3:19])=[CH:15][CH:14]=1>ClCCl>[Br:12][C:13]1[CH:21]=[CH:20][C:16]([CH2:17][N:18]([CH3:19])[C:8](=[O:10])[CH3:9])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 485400Benzenemethanamine, 4-bromo-N-methyl-

Product 1

HCID 12839032HCID 12839032, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of triethylamine (0.22 ml, 1.6 mmol) in dichloromethane (10 ml) was treated with acetyl chloride (0.08 ml, 1.10 mmol), followed by 4-bromo-N-methylbenzylamine (210 mg, 1.05 mmol). This mixture was then stirred under an atmosphere of argon for 10 minutes. The reaction mixture was washed twice with water and the organic layer was separated and dried over sodium sulphate, and the solvent removed via rotary evaporation to give a yellow oil which was purified on a 5 g sep-pak column eluting from 0-100% ethyl acetate in petroleum ether to give the title compound as a yellow oil.

Workup

  1. washThe reaction mixture was washed twice with water
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulphate
  4. customthe solvent removed via rotary evaporation
  5. customto give a yellow oil which
  6. customwas purified on a 5 g sep-pak column
  7. washeluting from 0-100% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-da55e3c108f24238a26d37eb5c3b3cd0
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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