Phosphoric Acid → 1-methyl-2-(3-piperidin-4-ylpropyl)-1H-benzimidazole

HRID 2074291Notes

Reaction equation

P(=O)(O)(O)O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:20][NH:21][C:22]1[C:23]([NH2:28])=[CH:24][CH:25]=[CH:26][CH:27]=1.Cl.[NH:30]1[CH2:35][CH2:34][CH:33]([CH2:36][CH2:37][CH2:38][C:39](O)=O)[CH2:32][CH2:31]1.[OH-].[Na+]>O>[CH3:20][N:21]1[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:28]=[C:39]1[CH2:38][CH2:37][CH2:36][CH:33]1[CH2:34][CH2:35][NH:30][CH2:31][CH2:32]1

Participants

Conditions

Temperature: 120 °C

Procedure

Phosphoric acid (7 ml) and diphosphorus pentoxide (14 g) were heated at 150° C. for 30 minutes, N-methylbenzene-1,2-diamine (1.3 g) and 4-piperidin-4-ylbutanoic acid hydrochloride (1.5 g) were added thereto, followed by heating at 120° C. for 3 hours. The reaction solution was poured into water, neutralized with aqueous sodium hydroxide solution, and then extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform:methanol:aqueous ammonia=10:1:0.1 (v/v/v)) to obtain 1-methyl-2-(3-piperidin-4-ylpropyl)-1H-benzimidazole (1.61 g).

Workup

extractionextracted with chloroform
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: chloroform:methanol:aqueous ammonia=10:1:0.1 (v/v/v))

Sources & evidence

ORD record: ord-976958549fd04664b7aaccda2aa80847
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919495B2

Reaction notes

Loading…