Morpholine, 4-(chloroacetyl)- → HCID 178521450, compound

HRID 2368130Notes

Reaction equation

HRID 2368130 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:21]=[CH:20][C:9]3[CH: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[CH: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 178521541HCID 178521541, compound

Product 1

HCID 178521450HCID 178521450, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of trans-4-[6-(cyclopropylmethoxy)-1-benzofuran-2-yl]cyclohexanol (611 mg), 4-(chloroacetyl)morpholine (1.05 g) and tert-butoxy potassium (718 mg) in THF (10 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 (882 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-b7569095f45042ba8d9be37b80a292c7
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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