Epichlorohydrin → 1-Chloro-3-morpholin-4-yl-propan-2-ol

HRID 731144

Reaction equation

HRID 731144 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]([CH:9]1[O:11][CH2:10]1)[Cl:8]>C(O)C>[Cl:8][CH2:7][CH:9]([OH:11])[CH2:10][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 8083Morpholine

Product 1

HCID 100809871-Chloro-3-morpholin-4-yl-propan-2-olYield 37.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of morpholine (2.6 mL, 30 mmol) and epichlorohydrin (2.35 ml, 30 mmol) in ethanol (50 mL) was stirred at 70° C. overnight. After removing the solvent, the residue was diluted with methylene chloride (50 mL). The clear solid precipitated was collected by vacuum filtration to give 1-chloro-3-morpholin-4-yl-propan-2-ol (2.0 g, 37%). 1H NMR (DMSO-d6) δ 3.49 (t, J=4.8 Hz, 2H), 3.60 (t, J=4.6 Hz, 2H), 3.75 (m, 4H, 2×CH2), 4.20 (dd, J=5.2, 12 Hz, 2H), 4.54 (m, 2H), 4.62 (m, 1H, CH), 6.64 (d, J=6.4 Hz, 1H, OH). MS (m/z) 180.2 (M+1).

Workup

  1. customAfter removing the solvent
  2. additionthe residue was diluted with methylene chloride (50 mL)
  3. customThe clear solid precipitated
  4. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-b01095e2f8aa421ca81e76b8c38f4d88
Source dataset
uspto-grants-2009_09
Patent number
US07582756B2

Linked notes

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