N-methyl-2-pyrrolidone → HCID 19752324, compound

HRID 1885315Notes

Reaction equation

HRID 1885315 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][N:8]=1)=[O:6].[F:16][C:17]1[CH:18]=[CH:19][C:20]2[C:24]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:23][S:22][C:21]=2[CH:31]=1.CN1CCCC1=O.[OH-].[Na+]>O>[ClH:1].[F:16][C:17]1[CH:18]=[CH:19][C:20]2[C:24]([N:25]3[CH2:26][CH2:27][N:28]([CH2:2][CH2:3][NH:4][C:5]([C:7]4[C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=5[O:9][N:8]=4)=[O:6])[CH2:29][CH2:30]3)=[CH:23][S:22][C:21]=2[CH:31]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 10242753HCID 10242753, compoundHCID 10609857HCID 10609857, compound

Product 1

HCID 19752324HCID 19752324, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of N-(2-chloroethyl)-1,2-benzisoxazole-3-carboxamide (4.40 g), 6-fluoro-3-(1-piperazinyl)benzo[b]thiophene (5.90 g), and N-methylpyrrolidinone (100 ml) was heated at 160° C. for 3.0 hr. The reaction mixture was allowed to cool, diluted with water (350 ml), basified with 25% sodium hydroxide to pH-8, and extracted with ether. The combined extracts were washed with water, brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The residue was chromatographed on silica gel, using 75% ethyl acetate in hexanes as the eluant. The appropriate fractions were collected and concentrated. Ethanolic hydrogen chloride was added to the residue. Recrystallization of the precipitate from methanol/ethanol gave 2.13 g (23.6%) of product, mp 225°-228° C. dec.

Workup

  1. temperatureto cool
  2. extractionextracted with ether
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. customThe appropriate fractions were collected
  9. concentrationconcentrated
  10. additionEthanolic hydrogen chloride was added to the residue
  11. customRecrystallization of the precipitate from methanol/ethanol

Sources & evidence

ORD record
ord-b596e518416847bebe723809a7aa9ec9
Source dataset
uspto-grants-1992_09
Patent number
US05143923

Reaction notes

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