Hydrogen chloride-ethyl acetate → HCID 71252049, compound

HRID 2411712Notes

Reaction equation

HRID 2411712 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][CH:26]([CH2:28][N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[CH2:25][C:24]3=[O:34])=[CH:19][CH:18]=2)=[O:16])[CH2:11][CH2:10]1.[ClH:35].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:35].[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH2:27][CH:26]([CH2:28][N:29]4[CH2:30][CH2:31][CH2:32][CH2:33]4)[CH2:25][C:24]3=[O:34])=[CH:21][CH:22]=2)=[O:16])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 71252050HCID 71252050, compound

Product 1

HCID 71252049HCID 71252049, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-{4-[4-(2,4-Dimethylphenyl)piperazine-1-carbonyl]phenyl}-4-hydroxymethylpyrrolidin-2-one (150 mg) described in Example 338 was dissolved in dichloromethane (2 mL), triethylamine (0.16 mL) and mesyl chloride (0.06 mL) were added, and the mixture was stirred at room temperature. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was dissolved in N,N-dimethylformamide (3 mL), pyrrolidine (0.15 mL) and potassium carbonate (51 mg) were added, and the mixture was stirred at 60° C.-70° C. for 9 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give 1-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}-4-(pyrrolidin-1-ylmethyl)pyrrolidin-2-one. The obtained 1-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}-4-(pyrrolidin-1-ylmethyl)pyrrolidin-2-one was dissolved in ethyl acetate, 4N hydrogen chloride/ethyl acetate (0.1 mL) was added, and the precipitate was collected by filtration to give the title compound (112 mg).

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-45642a5d71544ef98c6d2ffc218c96d6
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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