Potassium Carbonate → 4-(2-{4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]piperidin-1-yl}-2-oxoethyl)morpholine-3,5-dione

HRID 1873775Notes

Reaction equation

HRID 1873775 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[C:13]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)=[N:12]2)[CH2:7][CH2:6]1)=[O:4].[NH:29]1[C:34](=[O:35])[CH2:33][O:32][CH2:31][C:30]1=[O:36].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([C:13]2[C:14]([CH3:18])([CH3:17])[C:15](=[O:16])[N:11]([CH:8]3[CH2:7][CH2:6][N:5]([C:3](=[O:4])[CH2:2][N:29]4[C:34](=[O:35])[CH2:33][O:32][CH2:31][C:30]4=[O:36])[CH2:10][CH2:9]3)[N:12]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 364836Morpholine-3,5-dioneHCID 666166092-[1-(chloroacetyl)piperidin-4-yl]-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one2×

Product 1

HCID 251158444-(2-{4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]piperidin-1-yl}-2-oxoethyl)morpholine-3,5-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g 2-[1-(chloroacetyl)piperidin-4-yl]-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (compound A1), 0.5 g morpholine-3,5-dione and 1.0 g K2CO3 in 20 ml of DMF is heated for 17 h at 80-100° C. The DMF is removed in vacuo and the residue dissolved in 70 ml of DCM, washed four times with 30 ml of water and 20 ml of 0.5 M H2SO4. The DCM layer is dried over MgSO4 and concentrated in vacuo. The title product is crystallized from diethyl ether.

Workup

  1. customThe DMF is removed in vacuo
  2. dissolutionthe residue dissolved in 70 ml of DCM
  3. washwashed four times with 30 ml of water and 20 ml of 0.5 M H2SO4
  4. dry with materialThe DCM layer is dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe title product is crystallized from diethyl ether

Sources & evidence

ORD record
ord-73d19697a38f493783ef65f0d27233ff
Source dataset
uspto-grants-2012_11
Patent number
US08304436B2

Reaction notes

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