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

HRID 1837157Notes

Reaction equation

HRID 1837157 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-728689b4e2a94e7cbdbb0df13e37bd3a
Source dataset
uspto-grants-2004_08
Patent number
US06780878B2

Reaction notes

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