4-Methylmorpholine → 4-Butyl-4-methylmorpholin-4-ium bromide

HRID 1074212Notes

Reaction equation

HRID 1074212 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[CH2:8]([Br:12])[CH2:9][CH2:10][CH3:11]>C(C(C)=O)C>[Br-:12].[CH2:8]([N+:2]1([CH3:1])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1)[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 79724-MethylmorpholineHCID 8002Butyl bromide

Product 1

HCID 131238874-Butyl-4-methylmorpholin-4-ium bromideYield 23%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A sulfonating flask (250 ml) fitted with stirrer, drip funnel and reflux condenser is charged with 22.3 ml (0.2 mol) of N-methylmorpholine and 80 ml of methyl ethyl ketone (MEK), and then 21.4 ml (0.2 mol) of n-butyl bromide are added dropwise over 20 minutes. After initial turbidity under reflux conditions (ca. 80° C.), the reaction mixture becomes more dense and turns an orange-brown colour. After a reaction time of 7 hours, the crystalline slurry is filtered with suction and the filter residue is washed with a small amount of MEK and dried under vacuum. Yield: 23%; m.p. 205° C.

Workup

  1. customA sulfonating flask (250 ml) fitted with stirrer
  2. temperaturereflux condenser
  3. customunder reflux conditions (ca. 80° C.)
  4. filtrationAfter a reaction time of 7 hours, the crystalline slurry is filtered with suction
  5. washthe filter residue is washed with a small amount of MEK
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d57fdff7c0aa49458add09de2b95e287
Source dataset
uspto-grants-1990_11
Patent number
US04973648

Reaction notes

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