Potassium Permanganate → HCID 20239793, compound

HRID 1388403Notes

Reaction equation

HRID 1388403 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH2:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([CH:17]=[O:18])[CH2:13][CH2:12]2)[CH:5]=[CH:6][N:7]=1.[Mn]([O-])(=O)(=O)=[O:20].[K+]>CC(C)=O>[C:2]([C:3]1[N:4]([CH2:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([CH:17]=[O:18])[CH2:13][CH2:12]2)[CH:5]=[CH:6][N:7]=1)([OH:20])=[O:1]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 13726742HCID 13726742, compound

Product 1

HCID 20239793HCID 20239793, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

The solution of 4-[3-(2-hydroxymethyl-1H-imidazol-1-yl)propyl]-1-piperidine carboxaldehyde in acetone (63 ml) was cooled to 0° C. and potassium permanganate (5.5 g, 0.035 M) was added portionwise. After complete addition, the reaction was stirred at 0° C. for 2 hrs. The acetone solution was separated by filtration, and the residue was stirred twice with water (50 ml). The aqueous solution was freeze dried to yield 4-[3-(2-carboxy-1H-imidazol-1-yl)propyl]-1-piperidine carboxaldehyde (5.5 g, 83% yield). This product (7.1 g, 0.027 M) in water (26 ml) and 1 N NaOH (26 ml) was heated at 100° C. for 5 hrs. The reaction was adjusted pH 6 and purified on ion-exchange column (Bio-Rex 70) eluted with 0.01 N, 0.02 N, 0.04 N, 0.08 N and 0.1 N HCl solution successively to give 1-[3-(4-piperidinyl)propyl]-1H-imidazole-2-carboxylic acid 1.75 molar hydrochloride 0.65 molar hydrate (4.6 g, 73% yield).

Workup

  1. additionAfter complete addition
  2. customThe acetone solution was separated by filtration
  3. stirringthe residue was stirred twice with water (50 ml)
  4. customdried

Sources & evidence

ORD record
ord-27e1ccfad3f2408faa0b17d04e4386eb
Source dataset
uspto-grants-1984_02
Patent number
US04431653

Reaction notes

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