Morpholine → HCID 11659588, compound

HRID 2228444Notes

Reaction equation

HRID 2228444 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CS(C)=O.C(OCC)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 18469984HCID 18469984, compound

Product 1

HCID 11659588HCID 11659588, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 3-(4-aminophenyl)-1-(4-fluorophenyl)propan-1-one (0.56 g, 2.32 mmol) (prepared as described in Example 1b) and morpholine (1.01 g, 11.62 mmol) in dimethylsulfoxide (12 mL) was heated at 100-110° C. under nitrogen for about 12 hours. The reaction mixture was cooled, diluted with ethyl acetate (150 mL), washed with cold water and brine. The organic layer was separated, dried, and evaporated in vacuo to give the title compound as an oil which was used as such in the next step.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with cold water and brine
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-7701d1a89ed54d83981f58c95fb5828b
Source dataset
uspto-grants-2002_07
Patent number
US06417186B1

Reaction notes

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