Thionyl Chloride → Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

HRID 325984Notes

Reaction equation

HRID 325984 reaction equation
[N:1]1([CH2:7][CH2:8]O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.S(Cl)([Cl:12])=O>C1C=CC=CC=1>[ClH:12].[Cl:12][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 611632-Morpholinoethanol

Product 1

HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)Yield 151.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

In 2 l of benzene was dissolved 623 g of morpholine ethanol. The solution was stirred while maintaining its temperature below 35° C. with ice-cooling, followed by dropwise addition of 735 g of thionyl chloride in 500 ml of benzene. Upon completion of the dropping, the resultant mixture was refluxed with stirring for 4 hours. After cooling, the crystalline precipitate was collected to give 872.4 g (yield: 98.7%) of chloroethylmorpholine hydrochloride having a melting point of 180°-182° C.

Workup

  1. temperaturewhile maintaining its temperature below 35° C. with ice-
  2. temperaturecooling
  3. stirringwith stirring for 4 hours
  4. temperatureAfter cooling
  5. customthe crystalline precipitate was collected

Sources & evidence

ORD record
ord-8f6a3a08a04f42c5905d3b2efda0005e
Source dataset
uspto-grants-1984_04
Patent number
US04443603

Reaction notes

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