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

HRID 605785Notes

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-123727dc78614aca86a12bc3c0704b2e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915261B2

Reaction notes

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