Methanol → N-(3-Chloropropyl)-N,N-dimethyl-1-dodecanaminium bromide

HRID 2086510Notes

Reaction equation

HRID 2086510 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH3:3].[Br:16][CH2:17][CH2:18][CH2:19][Cl:20].CO>COC(C)(C)C>[Br-:16].[Cl:20][CH2:19][CH2:18][CH2:17][N+:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 80061-Bromo-3-chloropropaneHCID 8168Lauryldimethylamine2×

Product 1

HCID 10861601N-(3-Chloropropyl)-N,N-dimethyl-1-dodecanaminium bromide

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
65 °C

Procedure

A 2 L 3-neck round-bottom flask equipped with an air condenser and a magnetic stirrer was charged with N,N-dimethyldodecylamine (297.24 g), 1-bromo-3-chloropropane (220.44 g) and methanol (250 mL). The reaction was maintained at 65° C. for 24 hours. Methanol was removed by rotary evaporation under reduced pressure to yield a brown sludge. To the sludge was added methyl-tert-butylether (2 liters) causing a white solid to form. The mixture was stirred for two hours and a semi-crystalline, white particulate was collected by vacuum filtration. The particulate was dried in a vacuum oven at 35° C. for 24 hours. Yield 228.2 grams (0.61 moles, 44%). (4-Chlorobutyl)dodecyldimethylammonium bromide and (6-chlorohexyl)dodecyldimethylammonium bromide can be prepared by a similar process using the appropriate bromochloroalkane and dodecyldimethylamine.

Workup

  1. customA 2 L 3-neck round-bottom flask equipped with an air condenser and a magnetic stirrer
  2. customMethanol was removed by rotary evaporation under reduced pressure
  3. customto yield a brown sludge
  4. customto form
  5. filtrationa semi-crystalline, white particulate was collected by vacuum filtration
  6. customThe particulate was dried in a vacuum oven at 35° C. for 24 hours
  7. custom(4-Chlorobutyl)dodecyldimethylammonium bromide and (6-chlorohexyl)dodecyldimethylammonium bromide can be prepared by a similar process

Sources & evidence

ORD record
ord-a22e0c6068f3442a84b6ef9789892d02
Source dataset
uspto-grants-2004_04
Patent number
US06726905B1

Reaction notes

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