HCID 13281197, compound → 4-(1H-Imidazol-2-ylmethyl)piperidine

HRID 364729Notes

Reaction equation

HRID 364729 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)=[CH:3][CH:2]=1.O(C)[Na]>CO>[NH:9]1[CH:10]=[CH:11][N:12]=[C:8]1[CH2:7][CH:4]1[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 13281197HCID 13281197, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 132811984-(1H-Imidazol-2-ylmethyl)piperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(4-pyridylmethyl)imidazole (4 g, 0.025M) and platinum oxide (0.4 g) in ethanol (40 ml) and 2NHCl (50 ml) was hydrogenated at 45 psig for 4 hrs. The catalyst was removed by filtration and the filtrate was stripped to dryness. Crystallization from ethanol gave 4-(1H-imidazol-2-yl-methyl)piperidine as the dihydrochloride salt m.p. 251°-252° C. (5.2 g, 87% yield). The mixture of 2-(4-pyridylmethyl)-imidazole (2.38 g, 10 mM) and NaOCH3 (10 mM) in methanol (20 ml) was stirred for 10 min. and filtered. The filtrate was stripped to dryness and distilled from about 180° to about 200° C./0.3 mmHg to give the free base of 4-(1H-imidazol-2-yl-methyl)piperidine.

Workup

  1. filtrationfiltered
  2. distillationdistilled from about 180° to about 200° C./0.3 mmHg

Sources & evidence

ORD record
ord-9a1f8cc4ecdb4641921e3ff5378c2736
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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