Morpholine, 4-(chloroacetyl)- → HCID 178521451, compound

HRID 2368139Notes

Reaction equation

HRID 2368139 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:21]=[CH:20][C:9]3[N:10]=[C:11]([C@H:13]4[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.Cl[CH2:23][C:24]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:25].C(O[K])(C)(C)C>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:21]=[CH:20][C:9]3[N:10]=[C:11]([C@H:13]4[CH2:18][CH2:17][C@H:16]([O:19][CH2:23][C:24]([N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[O:25])[CH2:15][CH2:14]4)[O:12][C:8]=3[CH:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 74040Morpholine, 4-(chloroacetyl)-HCID 178418922HCID 178418922, compoundHCID 178521554HCID 178521554, compound

Product 1

HCID 178521451HCID 178521451, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of trans-4-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]cyclohexanol (311 mg), 4-(chloroacetyl)morpholine (532 mg) and tert-butoxy potassium (365 mg) in THF (5 mL) was stirred at room temperature overnight and extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (427 mg).

Workup

  1. extractionextracted with ethyl acetate and water
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5c7f9c4ff6e64cb6a72d91abb57c7c35
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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