Water → HCID 18324770, compound

HRID 1250829Notes

Reaction equation

HRID 1250829 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:12]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[N:9]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:30][CH:31]1[CH2:34][CH2:33][CH2:32]1.O>CN(C=O)C>[CH:31]1([CH2:30][N:16]2[CH2:15][CH2:14][CH:13]([N:12]3[C:11]4[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=4[N:9]=[C:8]3[N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[CH2:18][CH2:17]2)[CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 2734658(Bromomethyl)cyclobutane2×HCID 18324765HCID 18324765, compound

Product 1

HCID 18324770HCID 18324770, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-methylpiperazinyl)-1-(4-piperidinyl)-1H-benzimidazole (300 mg, 1 mmol), K2CO3 (165.9 mg, 1.2 mmol), and (bromomethyl)cyclobutane (178.8 mg, 1.2 mmol) in DMF (4 ml) was stirred at room temperature for 17 h. Then K2CO3 (110 mg, 0.8 mmol), and (bromomethyl)cyclobutane (119 mg, 0.8 mmol) were added to the reaction mixture. After 16 h stirring, the reaction mixture was poured into water and extracted with CH2Cl2. The extracts combined were dried (MgSO4), filtered, and concentrated in vacuo to give 369 mg of oil which was purified by preparative TLC (1 mm thick plate, CH2Cl2/MeOH:10/12 developped) to afford 147.6 mg (40%) of title compound as light brown solid.

Workup

  1. stirringAfter 16 h stirring
  2. extractionextracted with CH2Cl2
  3. dry with materialThe extracts combined were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca6dd3ff60b345bf85be271dc35016c0
Source dataset
uspto-grants-2002_01
Patent number
US06340681B1

Reaction notes

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