Dimethylformamide → 2-Hydroxy-N,N-dimethyl-N-octylcyclohexan-1-aminium bromide

HRID 441436Notes

Reaction equation

HRID 441436 reaction equation
[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[OH:9].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].CN(C)C=O>CC1C=CC(C)=CC=1>[Br-:11].[OH:9][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH:3]1[N+:2]([CH3:10])([CH3:1])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 81401-BromooctaneHCID 978902-(Dimethylamino)cyclohexanol

Product 1

HCID 706357442-Hydroxy-N,N-dimethyl-N-octylcyclohexan-1-aminium bromide

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A solution comprising 5 g of 2-dimethylamino-1-cyclohexanol, 10 g of 1-bromooctane and 5 ml of dimethylformamide was heated in a glass pressure bottle at about 95° for 16 hours. p-Xylene (25 ml) was added and the solution was concentrated at 60° using a film evaporator to remove dimethylformamide as its azeotrope with xylene. A second 25 ml portion of p-xylene was added and the azeotrope distilled until the residue was free of volatile material. This residue was dissolved in water, and the aqueous solution was extracted five times with diethyl ether. The aqueous solution was then concentrated under reduced pressure to give (2-hydroxycyclohexyl)(dimethyl)octylammonium bromide, a clear amorphous gum.

Workup

  1. temperaturewas heated in a glass pressure bottle at about 95° for 16 hours
  2. concentrationthe solution was concentrated at 60°
  3. customa film evaporator
  4. customto remove dimethylformamide as its azeotrope with xylene
  5. additionA second 25 ml portion of p-xylene was added
  6. distillationthe azeotrope distilled until the residue
  7. dissolutionThis residue was dissolved in water
  8. extractionthe aqueous solution was extracted five times with diethyl ether
  9. concentrationThe aqueous solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-b9693709d82a4860987f2c6986d28f01
Source dataset
uspto-grants-1977_08
Patent number
US04040813

Reaction notes

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