4-Methylmorpholine → [4-(Morpholin-4-yl)phenyl]methanol

HRID 2084294

Reaction equation

HRID 2084294 reaction equation
[N:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O.CO>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][OH:12])=[CH:14][CH:15]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 3452784-(Morpholin-4-yl)benzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 2776456[4-(Morpholin-4-yl)phenyl]methanolYield 18%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4-morpholinyl)benzoic acid (1.00 g, 4.83 mmol) and 4-methylmorpholine (0.53 mL, 4.8 mmol) in tetrahydrofuran (25 mL) at −10° C. was treated with ethyl chloroformate (0.46 mL, 4.8 mmol). After 0.25 h, the mixture was treated with sodium borohydride (550 mg, 14.5 mmol) followed by MeOH (50 mL) slowly. The mixture was then treated with 5% HOAC in water and the mixture was concentrated . The residue was purified by chromatography (SiO2, EtOAc:hexanes) yielding 164 mg (18%) of the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by chromatography (SiO2, EtOAc:hexanes)

Sources & evidence

ORD record
ord-b8e3b5d908134d1b83dcd750c12c9c25
Source dataset
uspto-grants-2004_04
Patent number
US06716855B2

Linked notes

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