Triethylamine → 5-{N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylaminocarbonyl}-pentyl bromide

HRID 1078348Notes

Reaction equation

HRID 1078348 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[CH3:10][NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1.C(N(CC)CC)C>ClCCl.C1(C)C=CC=CC=1>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([CH2:13][CH2:12][N:11]([CH3:10])[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[O:8])[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77039N-MethylhomoveratrylamineHCID 898486-Bromohexanoyl chloride

Product 1

HCID 229023315-{N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylaminocarbonyl}-pentyl bromide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

10 ml of 6-bromohexanoyl chloride were dissolved in a mixture of 100 ml of absolute dichloromethane and 100 ml of absolute toluene. A solution of 13.6 g of N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-amine and 9.5 ml of triethylamine in 25 ml of absolute toluene was added dropwise to the solution with ice cooling. The reaction mixture was subsequently stirred at room temperature for 12 hours. In order to work it up, the precipitated salts were filtered out and washed with toluene. The filtrate was washed first with 1 molar citric acid solution and then with sodium bicarbonate solution, dried with magnesium sulfate and concentrated. 19.3 g of 5-{N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylaminocarbonyl}-pentyl bromide were obtained as an oil.

Workup

  1. filtrationthe precipitated salts were filtered out
  2. washwashed with toluene
  3. washThe filtrate was washed first with 1 molar citric acid solution
  4. dry with materialwith sodium bicarbonate solution, dried with magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b2a2b785f3234312b084b7c66fc5c0cc
Source dataset
uspto-grants-1996_08
Patent number
US05547967

Reaction notes

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