Potassium Carbonate → Ipsapirone

HRID 330228Notes

Reaction equation

HRID 330228 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[S:7]1(=[O:17])=[O:16].[N:18]1[CH:23]=[CH:22][CH:21]=[N:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[N:18]1[CH:23]=[CH:22][CH:21]=[N:20][C:19]=1[N:24]1[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:10](=[O:11])[C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[S:7]2(=[O:17])=[O:16])[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 887471-(2-Pyrimidinyl)piperazineHCID 107817741,1-Dioxido-2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-one

Product 1

HCID 56971Ipsapirone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.02 mole o& 2-(4-bromobutyl)-1,2-benzoisothiazol-3-(2H)-one 1,1-dioxide and 0.02 mole of 1-(2-pyrimidyl)piperazine are stirred with 0.02 mole of K2CO3 in 150 ml of absolute dimethylformamide (DMF) at 100° C. for 1 hour. The mixture is then concentrated. Water is added and the organic substance is taken up in methylene chloride (CH2Cl2). The dried CH2Cl2 phase is applied to a silica gel column and eluted with CH2Cl2 /CH3OH (95:5).

Workup

  1. concentrationThe mixture is then concentrated
  2. additionWater is added
  3. washeluted with CH2Cl2 /CH3OH (95:5)

Sources & evidence

ORD record
ord-eb678b103b5a4f11b271683e5db34a9d
Source dataset
uspto-grants-1990_01
Patent number
US04895848

Reaction notes

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