Morpholine, 4-(chloroacetyl)- → HCID 59202065, compound

HRID 1624191Notes

Reaction equation

HRID 1624191 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].Cl[CH2:10][C:11]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12]>CN1CCCC1=O>[N:13]1([C:11](=[O:12])[CH2:10][O:5][C:4](/[CH:3]=[CH:2]/[C:1]([OH:8])=[O:7])=[O:6])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 74040Morpholine, 4-(chloroacetyl)-HCID 444972Fumaric Acid

Product 1

HCID 59202065HCID 59202065, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following general procedure A, fumaric acid (1.00 g, 8.60 mmol) was reacted with chloro acetyl morpholine (1.4 g, 8.6 mmol) and Ag2O (4.2 g, 9.47 mmol) at ca. 100° C. in N-methylpyrrolidinone. The reaction mixture was cooled to room temperature, filtered over Celite®, and the filter cake was washed with ethylacetate (EtOAc). The combined organic filtrates were subjected to acidic aqueous work-up and the crude material was purified by mass-guided preparative HPLC to give 0.50 g (24% yield) of the title compound (47) as a white solid. 1H NMR (CD3CN, 400 MHz): δ 6.85-6.80 (m, 2H), 4.85 (s, 2H), 3.64-3.60 (m, 4H), 3.57-3.54 (t, J=4.8 Hz, 2H), 3.42-3.39 (t, J=5.2 Hz, 2H). MS (ESI): m/z 244.06 (M+H)+, 242.07 (M−H)−.

Workup

  1. filtrationfiltered over Celite®
  2. washthe filter cake was washed with ethylacetate (EtOAc)
  3. customthe crude material was purified by mass-guided preparative HPLC

Sources & evidence

ORD record
ord-6039f07976a64add99306c5440d9c640
Source dataset
uspto-grants-2014_07
Patent number
US08778991B2

Reaction notes

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