4-Methylmorpholine → HCID 59149862, compound

HRID 655554Notes

Reaction equation

HRID 655554 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:11][C@@H:12]1[NH:17][CH2:16][CH2:15][N:14]([CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:13]1=[O:27].CN1CCOCC1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([N:17]2[CH2:16][CH2:15][N:14]([CH2:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[C:13](=[O:27])[C@@H:12]2[CH3:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 67079895HCID 67079895, compound2×

Product 1

HCID 59149862HCID 59149862, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chlorophenyl isocyanate (36 mg, 0.23 mmol) was added to a solution of (S)-3-methyl-1-(3-piperidin-1-yl-propyl)-piperazin-2-one (intermediate 20; 52 mg, 0.21 mmol) and 4-methylmorpholine (21 mg, 0.21 mmol) in N,N-dimethylformamide (1 ml), then after 16 h the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; dichloro-methane/methanol/25% aq. ammonia solution 90:10:0.25) produced the title compound (68 mg, 84%). Colorless gum, MS (ISP)=393.2 (M+H)+.

Workup

  1. customafter 16 h the reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-cdf66932fb354b7baf136d37932db783
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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