Morpholine → HCID 68906069, compound

HRID 1785733Notes

Reaction equation

HRID 1785733 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:28]([F:31])([F:30])[F:29])=[C:11]([CH2:15][O:16][CH:17]3[CH2:20][N:19]([C:21]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]3)[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>>[N:32]1([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[C:10]([C:28]([F:31])([F:30])[F:29])=[C:11]([CH2:15][O:16][CH:17]4[CH2:20][N:19]([C:21]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]4)[CH:12]=[CH:13][CH:14]=3)=[CH:5][CH:4]=2)[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 68907467HCID 68907467, compound

Product 1

HCID 68906069HCID 68906069, compoundYield 70%

Procedure

The benzyl chloride (195) (40 mg, 0.088 mmol) and morpholine (3 mL, 31 mmol) were heated to 50° C. for 18 h. The reaction mixture was cooled, excess amine was removed under reduced pressure and the residue partitioned between ethyl acetate and sodium hydroxide (1M). The organic phase was washed with water (2×20 mL) and brine (20 mL), dried (Na2SO4), filtered and the solvent removed under reduced pressure to afford the crude product. Purification by SCX-2 cartridge afforded the title compound (196) as a white solid (31 mg, 70% yield).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customexcess amine was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and sodium hydroxide (1M)
  4. washThe organic phase was washed with water (2×20 mL) and brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customto afford the crude product
  9. customPurification by SCX-2 cartridge

Sources & evidence

ORD record
ord-d2f1392018114bdfb8d2b6298aa1e4bd
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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