1-Methylpiperazine → HCID 18324767, compound

HRID 1250827Notes

Reaction equation

HRID 1250827 reaction equation
Cl[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:9][CH2:8]2)[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[N:3]=1.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>CO>[CH:14]1([CH2:13][N:10]2[CH2:11][CH2:12][CH:7]([N:6]3[C:5]4[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=4[N:3]=[C:2]3[N:27]3[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]3)[CH2:8][CH2:9]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 17801669HCID 17801669, compound

Product 1

HCID 18324767HCID 18324767, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 1-(1-cyclopentylmethyl-4-piperidinyl)-1,3-dihydro-2H-benzimidazole-2-one(202 mg) and POCl3(5 ml) was heated at 120° C. for 2 h. After cooling down to room temperature, the reaction mixture was poured into NH4OH solution, and extracted with CH2Cl2. The extracts combined were washed with water, and dried (Na2SO4). After filtration, the filtrate was concentrated to give oil, which was purified by preparative TLC (1 mm thick plate×2, CH2Cl2/MeOH:15/1) to give 148 mg (69%) of 2-chloro-1-(1-cyclopentylmethyl-4-peridinyl)-1H-benzimidazole as colorless amorphous solid. To a solution of 2-chloro-1-(1-cyclopentylmethyl-4-piperidinyl)-1H-benzimidazole(148 mg, 0.466 mmol) in MeOH(5 ml) was added N-methylpiperazine(1 ml) and the resulting mixture was heated at 120° C. in a sealed tube for 2 days. After concentration, the residue was purified by preparative TLC (1 mm thick plate×2, CH2Cl2/MeOH:12/1, 2 developed) to give 161 mg of colorless amorphous solid. This was purified again by column chromatography(basic silica gel: 50 g; CH2Cl2/MeOH:200/1 to 50/1) to afford 52 mg (29%) of title compound as colorless amorphous solid.

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by preparative TLC (1 mm thick plate×2, CH2Cl2/MeOH:12/1, 2 developed)

Sources & evidence

ORD record
ord-5203a923c5ab4374a6ec26edeac69801
Source dataset
uspto-grants-2002_01
Patent number
US06340681B1

Reaction notes

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