Diethyl Ether → 1-Dodecanaminium, N-(2-hydroxyethyl)-N,N-dimethyl-, bromide (1:1)

HRID 436151Notes

Reaction equation

HRID 436151 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].CC[O:9]CC.[CH2:12]([N:16]=[C:17]=[O:18])[CH2:13][CH2:14][CH3:15].[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C(OCC)(=O)C>[Br-:19].[OH:5][CH2:4][CH2:3][N+:2]([CH3:6])([CH3:1])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[CH2:12]([NH:16][C:17](=[O:9])[O-:18])[CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 3283Diethyl Ether2×HCID 79022-(Dimethylamino)ethanolHCID 8110Butyl isocyanateHCID 89191-Bromododecane

Product 2

HCID 814861-Dodecanaminium, N-(2-hydroxyethyl)-N,N-dimethyl-, bromide (1:1)HCID 5247103HCID 5247103, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-hydroxyethyldimethyldodecylammonium bromide, N-butylcarbamate is prepared in the following manner: A solution of 58 g. (0.65 mole) 2-dimethylaminoethanol in 150 ml. ether was treated over a period of 1.5 hours with 70 g. (0.71 mole) n-butyl isocyanate. After stirring another two hours the reaction mixture was stripped of ether and distilled in vacuum. The product, 2-dimethylaminoethyl N-butylcarbamate was collected at 106°/1.2 Torr. For quaternization 75 g. (0.40 mole) of the above prepared amine was combined with 105 g (0.42 mole) 1-bromododecane and allowed to stand stoppered for nine days. At this time the reaction mixture was a stiff gel with some crystalline portions. By solution in ethyl acetate (900 ml.) and chilling, 160 g. of product was obtained in crystalline form. After two more recrystallizations from ethyl acetate, the material melted at 64° C. to liquid crystals and to a liquid at 115° C.

Workup

  1. distillationdistilled in vacuum
  2. customThe product, 2-dimethylaminoethyl N-butylcarbamate was collected at 106°/1.2 Torr
  3. custom(0.40 mole) of the above prepared amine
  4. waitto stand stoppered for nine days
  5. customof product was obtained in crystalline form
  6. customAfter two more recrystallizations from ethyl acetate
  7. customat 115° C.

Sources & evidence

ORD record
ord-cf5d64ecdde6408584c556714dee043d
Source dataset
uspto-grants-1977_02
Patent number
US04007281

Reaction notes

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