Ethanol → 4-Morpholinehexanol

HRID 644787Notes

Reaction equation

HRID 644787 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].C(O)C.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[OH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 779706-Bromo-1-hexanol

Product 1

HCID 222185044-MorpholinehexanolYield 98.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of morpholine (3.30 mL, 3.30 g, 37.8 mmol), 6-bromo-1-hexanol (6.72 g, 72.3 mmol), ethanol (20 mL), and potassium carbonate (6.23 g, 45.1 mmol) was stirred for 36 hours at 25° C., after a slight exotherm at the beginning. The reaction mixture was diluted with ethyl acetate (30 mL), filtered and concentrated. The residue was taken up in ethyl acetate, filtered and concentrated. The 7.0 g of 4-(6-hydroxyhexyl)morpholine was isolated as a yellow oil and used as is.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-37690b49f28f4a21958d402ccc1b59d7
Source dataset
uspto-grants-2010_04
Patent number
US07700775B2

Reaction notes

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