Tetrahydrofuran → Risperidone

HRID 969737Notes

Reaction equation

HRID 969737 reaction equation
[H-].[Na+].O1CCCC1.F[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16](=[N:37][OH:38])[CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[C:30](=[O:31])[N:29]3[CH2:32][CH2:33][CH2:34][CH2:35][C:28]3=[N:27][C:26]=2[CH3:36])[CH2:19][CH2:18]1>O>[F:15][C:13]1[CH:12]=[CH:11][C:10]2[C:16]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]4[C:30](=[O:31])[N:29]5[CH2:32][CH2:33][CH2:34][CH2:35][C:28]5=[N:27][C:26]=4[CH3:36])[CH2:19][CH2:18]3)=[N:37][O:38][C:9]=2[CH:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 71433889Risperidal iMpurity B

Product 1

HCID 5073RisperidoneYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 40 mg (0.9166 millimole) of 55% sodium hydride and 2 ml of tetrahydrofurane 0.1089 g (0.2532 millimole) of 3-[2-[4-[(2,4-difluorophenyl)-(hydroxyimino)-methyl]-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one is added. The reaction mixture is heated to boiling for an hour, whereupon 5 ml of water are added and the mixture is extracted twice with 10 ml of dichloromethane each. The combined organic phases are dried over magnesium sulfate and evaporated in vacuo. Thus 80 mg of the title compound are obtained, yield 77%. According to HPLC analysis the purity of the product is 97.5%.

Workup

  1. additionis added
  2. temperatureThe reaction mixture is heated
  3. additionare added
  4. extractionthe mixture is extracted twice with 10 ml of dichloromethane each
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-08ce3ee00e0c4bee98be53ed511da509
Source dataset
uspto-grants-2007_12
Patent number
US07307168B2

Reaction notes

Loading…