Hydrochloric Acid → 3-(1H-imidazol-2-yl)piperidine hydrochloride

HRID 659621Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]1[CH2:11][CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7]1.Cl.C(Cl)[Cl:24].CO>O1CCOCC1>[ClH:24].[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]1[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1

Participants

Conditions

Temperature: 70 °C

Procedure

A 250-mL round-bottomed flask was charged with a solution of benzyl 3-(1H-imidazol-2-yl)piperidine-1-carboxylate (1.5 g, 5.26 mmol, 1.00 equiv) in dioxane (15 mL). To this was added conc. HCl (9 mL). The resulting mixture was stirred for 4 hours at 70° C. in an oil bath. The reaction progress was monitored by TLC (DCM: MeOH=10:1). Upon completion, the resulting solution was diluted with dioxane (10 mL) and concentrated on a rotary evaporator affording 3-(1H-imidazol-2-yl)piperidine hydrochloride as black solid in (0.48 g, 57%).

Workup

concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record: ord-a959826435da479dabb1297263d49589
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080566B1

Reaction notes

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