3-Chloro-1,2-propanediol → 3-Morpholinopropane-1,2-diol

HRID 1263046Notes

Reaction equation

HRID 1263046 reaction equation
Cl[CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>>[O:10]1[CH2:11][CH2:12][N:7]([CH2:2][CH:3]([OH:6])[CH2:4][OH:5])[CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 72903-Chloro-1,2-propanediol2×HCID 8083Morpholine2×

Product 1

HCID 1108503-Morpholinopropane-1,2-diolYield 75.5%

Conditions

Temperature
80 °C

Procedure

33 g of 3-chloropropylene glycol was added dropwise to 65 g morpholine, with stirring, while maintaining the temperature at 80° C. The 3-chloropropylene glycol reacted quickly with the morpholine exothermically. The reaction mixture was stirred for 3 hours, with the temperature maintained at 80° C. The salt of morpholine, which separated from the reaction mixture, was filtered out. The filtrate was distilled under reduced pressure. This distillation gave 35 g of the desired product, 3-morpholino propylene glycol (bp. 135°-138° C./11 mmHg), in a 75.5% yield.

Workup

  1. stirringThe reaction mixture was stirred for 3 hours, with the temperature
  2. temperaturemaintained at 80° C
  3. customThe salt of morpholine, which separated from the reaction mixture
  4. filtrationwas filtered out
  5. distillationThe filtrate was distilled under reduced pressure
  6. distillationThis distillation

Sources & evidence

ORD record
ord-81c312e80e72458991763699622137fc
Source dataset
uspto-grants-1984_06
Patent number
US04455168

Reaction notes

Loading…