Morpholine → 3-Morpholino-1-propanol

HRID 1434853Notes

Reaction equation

HRID 1434853 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]>C(Cl)Cl>[N:1]1([CH2:8][CH2:9][CH2:10][OH:11])[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 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a mixture of morpholine (33 mL, 371 mmol) and CH2Cl2 (650 mL) was added 3-bromopropanol (25.8 g, 186 mmol), and the mixture was heated at 50° C. for 18 h. The reaction was cooled, diluted with CH2Cl2, and filtered. The filtrate was chromatographed (150 g SiO2, CH2Cl2 to 5% 2 M NH3/MeOH in CH2Cl2) to give the title compound as a liquid (27.0 g, 50%).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customThe filtrate was chromatographed (150 g SiO2, CH2Cl2 to 5% 2 M NH3/MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-7b4a6260c4f54d6093fb17a5aec65138
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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