Morpholine → 4-(8-Hydroxyoctyl)morpholine

HRID 1593661Notes

Reaction equation

HRID 1593661 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[OH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 1626071-Octanol, 8-bromo-HCID 516892Sodium Bicarbonate

Product 1

HCID 222185134-(8-Hydroxyoctyl)morpholineYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.0 g (47.8 mmol) of 8-bromo-1-octanol, 10.41 g (120 mmol) of morpholine and tetrahydrofuran was heated to reflux for 3 hr. The cooled reaction mixture was treated with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and concentrated to give 10.50 g of 4-(8-hydroxyoctyl)morpholine.

Workup

  1. temperatureto reflux for 3 hr
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d557d1c10d0e40758211f2bb5da8de17
Source dataset
uspto-grants-2007_11
Patent number
US07297794B2

Reaction notes

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