Morpholine → 3-Morpholino-1-propanol

HRID 454062Notes

Reaction equation

HRID 454062 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][CH2:9][CH2:10][OH:11]>C1(C)C=CC=CC=1>[OH:11][CH2:10][CH2:9][CH2:8][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 123083-Bromo-1-propanol

Product 1

HCID 1995763-Morpholino-1-propanolYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Morpholine (94 g, 1.08 mol) was added dropwise to a solution of 3-bromo-1-propanol (75 g, 0.54 mol) in toluene (750 ml) and the reaction then heated at 80° C. for 4 hours. The mixture was allowed to cool to ambient temperature and the precipitated solid was removed by filtration. The volatiles were removed from the filtrate and the resulting yellow oil was purified by distillation at 0.4-0.7 mmHg to give 4-(3-hydroxypropyl)morpholine (40 g, 50%) as a colourless oil.

Workup

  1. customthe reaction
  2. temperatureto cool to ambient temperature
  3. customthe precipitated solid was removed by filtration
  4. customThe volatiles were removed from the filtrate
  5. distillationthe resulting yellow oil was purified by distillation at 0.4-0.7 mmHg

Sources & evidence

ORD record
ord-05f4a86773f24d2ebafe16dd4247a153
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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