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

HRID 1388394Notes

Reaction equation

HRID 1388394 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, 0.025 M) and platinum oxide (0.4 g) in ethanol (40 ml) and 2 NHCl (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-5be952032a6440e1a03660fd27796aa7
Source dataset
uspto-grants-1984_02
Patent number
US04431653

Reaction notes

Loading…