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

HRID 485804Notes

Reaction equation

HRID 485804 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-81f2a1beeac944179cae2451e3f52f46
Source dataset
uspto-grants-1985_08
Patent number
US04537969

Reaction notes

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