Water → 1-{3-[4-(5-Chloro-pyridin-2-yl)-piperazin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one

HRID 1418319Notes

Reaction equation

HRID 1418319 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:15][CH2:16][CH2:17][N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[NH:20][C:19]1=[O:27].C(N(C(C)C)CC)(C)C.O>CN(C=O)C.C1(C)C=CC=CC=1>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([N:1]2[CH2:2][CH2:3][N:4]([CH2:15][CH2:16][CH2:17][N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[NH:20][C:19]3=[O:27])[CH2:5][CH2:6]2)=[N:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 38053011-(5-Chloropyridin-2-yl)piperazine

Product 1

HCID 98857851-{3-[4-(5-Chloro-pyridin-2-yl)-piperazin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-oneYield 116.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.14 gm of 2-piperazino 5-chloro pyridine, 1.35 gm of 1-(3-chloro propyl)-2,3-dihydro-1H-benzimidazol-2-one (available from Janssen) and 1.49 gm of diisopropylethylamine in 3 ml DMF and 30 ml toluene is kept for 12 hours at 110° C. Upon cooling to ambient temperature, 30 ml water is added and the mixture is extracted with chloroform (CHCl3) and the extract is collected, washed with 20 ml water and dried over sodium sulfate (Na2SO4). The crude product (2.5 gm) which is obtained after removing the solvents is purified using chromatography: solid phase (SiO2 ; 40 μm; Baker); eluant 2% methanol (CH3OH) in methylene chloride (CH2Cl2). A sample of this purified material (1.2 gm) was transferred into its hydrochloride (mp: 200° C.) by treating an ethanolic suspension of this material with a mixture of ethyl ether/HCl.

Workup

  1. extractionthe mixture is extracted with chloroform (CHCl3)
  2. customthe extract is collected
  3. washwashed with 20 ml water
  4. dry with materialdried over sodium sulfate (Na2SO4)

Sources & evidence

ORD record
ord-9a87f6a3a8764ef8a645bbcb9442a8c5
Source dataset
uspto-grants-1999_03
Patent number
US05883094

Reaction notes

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