Morpholine → HCID 67046594, compound

HRID 606571Notes

Reaction equation

HRID 606571 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]([C:10]1[S:11][C:12]([Br:15])=[CH:13][CH:14]=1)(=O)[CH3:8].[BH4-].[Na+]>[OH-].[Na+].CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:15][C:12]1[S:11][C:10]([CH:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH3:8])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 793352-Acetyl-5-bromothiopheneHCID 4311764Sodium borohydride

Product 1

HCID 67046594HCID 67046594, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of morpholine (1.20 mmol) in titanium (IV) isopropoxide (1.95 mmol) was added 2-acetyl-5-bromothiophene (1.20 mmol). The reaction was heated in a microwave at 150° C. for 5 minutes. Sodium borohydride (1.95 mmol) was added and the reaction stirred at RT for 16 h. The reaction was diluted with sodium hydroxide solution (2N, 10 ml) and the solids formed removed by filtration. The filtrate was extracted with ethylacetate (3×20 ml), the combined organics were washed with brine and dried over magnesium sulphate. The product was purified by flash chromatography (silica gel, 10-20% ethylacetate in iso-hexane) to, give the title product as a brown oil: m/z=276 (100%, M+H), 278 (100%, M+H) in MS ES+.

Workup

  1. customthe solids formed
  2. customremoved by filtration
  3. extractionThe filtrate was extracted with ethylacetate (3×20 ml)
  4. washthe combined organics were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customThe product was purified by flash chromatography (silica gel, 10-20% ethylacetate in iso-hexane) to,

Sources & evidence

ORD record
ord-a861c8a6178240cd85482c45d75db8a6
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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