Morpholine → HCID 68512221, compound

HRID 1716276Notes

Reaction equation

HRID 1716276 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]1[CH2:14][CH:13]=[C:12]([CH2:15]Cl)[CH2:11][N:10]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])([CH3:4])([CH3:3])[CH3:2].[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C(#N)C>[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]1[CH2:14][CH:13]=[C:12]([CH2:15][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:11][N:10]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 68512996HCID 68512996, compound

Product 1

HCID 68512221HCID 68512221, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 234 mg of (1-Benzyloxy-6-chloromethyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-carbamic acid tert-butyl ester in 10 mL of acetonitrile was added 0.5 mL of morpholine. The mixture was heated to 65° C. for 2 hours. The reaction was cooled and the mixture was extracted with ethyl acetate. The organic layer was washed with NaHCO3(aq.) and NaCl (aq.) solutions. The aqueous layers were re-extracted with ethyl acetate, and the organic layers were combined and dried over Na2SO4(s). Filtration and solvent removal gave 270 mg of a clear oil. MS: 454 (M+Na), 432 (M+H).

Workup

  1. temperatureThe reaction was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with NaHCO3(aq.) and NaCl (aq.) solutions
  4. extractionThe aqueous layers were re-extracted with ethyl acetate
  5. dry with materialdried over Na2SO4(s)
  6. filtrationFiltration and solvent removal

Sources & evidence

ORD record
ord-c664fef8666048b0a162944f67aac0bb
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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