Morpholine → HCID 86718434, compound

HRID 1523408Notes

Reaction equation

HRID 1523408 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:25]=[CH:24][C:9]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:8][C:7]=1[F:26])=[O:4].[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:26][C:7]1[CH:8]=[C:9]([CH:24]=[CH:25][C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[O:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 86718433HCID 86718433, compound

Product 1

HCID 86718434HCID 86718434, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tert-Butyl 4-[4-(2-Chloro acetylamino)-3-fluoro phenoxy]piperidine-1-carboxylate (3.31 g, 0.0085 moles, obtained in preparation 3), morpholine (0.89 g, 0.01 moles) and potassium carbonate (1.75 g, 0.012 moles) in acetonitrile (30 mL) was stirred for 5 hours at reflux temperature. The mixture was concentrated under reduced pressure and the residue, thus obtained, was partitioned between ethyl acetate (50 mL) and water (50 mL). The resulted aq. Phase was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine solution, dried over sodium sulfate and concentrated. The crude compound was purified by flash chromatography (ethyl acetate:hexane, 3:7) to obtain the title compound 3.1 g (Yield: 83.5%).

Workup

  1. temperatureat reflux temperature
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue, thus obtained
  4. customwas partitioned between ethyl acetate (50 mL) and water (50 mL)
  5. extractionThe resulted aq. Phase was extracted with ethyl acetate (2×50 mL)
  6. washThe combined organic layers were washed with brine solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude compound was purified by flash chromatography (ethyl acetate:hexane, 3:7)

Sources & evidence

ORD record
ord-6aad97583e40400a9a07252d1d8347d1
Source dataset
uspto-grants-2015_07
Patent number
US09079888B2

Reaction notes

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