Chloroform → 4-(4-Chlorobutyl)-2,6-dimethylmorpholine hydrochloride

HRID 2255376Notes

Reaction equation

HRID 2255376 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH:10]([CH3:12])[O:9][CH:8]([CH3:13])[CH2:7]1.C(Cl)(Cl)[Cl:15].S(Cl)([Cl:20])=O>C(OCC)C>[ClH:15].[Cl:20][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH:10]([CH3:12])[O:9][CH:8]([CH3:13])[CH2:7]1

Participants

5

Reactant 3

HCID 6212Chloroform2×HCID 24386Thionyl ChlorideHCID 197380294-(4-Hydroxybutyl)-2,6-dimethylmorpholine

Product 1

HCID 197380244-(4-Chlorobutyl)-2,6-dimethylmorpholine hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

To a dry flask under a nitrogen atmosphere was added 0.9 g. (4.8 mmoles) of 4-(4-hydroxybutyl)-2,6-dimethylmorpholine in 2.5 ml. of chloroform. The solution was stirred and heated to 40° C. and 0.49 ml. (6.72 mmoles) of thionyl chloride in 2.5 ml. of chloroform was added slowly. The mixture was slowly heated to reflux and held for two hours, then was cooled and diluted with diethyl ether to precipitate the crude product. The crystals were filtered and washed of residual thionyl chloride using diethyl ether to obtain 1.0 g. (85% yield) of 4-(4-chlorobutyl)-2,6-dimethylmorpholine hydrochloride.

Workup

  1. additionTo a dry flask under a nitrogen atmosphere was added 0.9 g
  2. temperatureThe mixture was slowly heated
  3. temperatureto reflux
  4. temperaturewas cooled
  5. customto precipitate the crude product
  6. filtrationThe crystals were filtered
  7. washwashed of residual thionyl chloride
  8. customto obtain 1.0 g

Sources & evidence

ORD record
ord-f2ba384b21ac49138a7e7f460cba5cde
Source dataset
uspto-grants-1993_08
Patent number
US05240925

Reaction notes

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