Pyridine → HCID 178447559, compound

HRID 614835Notes

Reaction equation

HRID 614835 reaction equation
[OH:1][CH:2]([CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17][CH2:16]1)[CH2:3][O:4][C:5]1[C:13]2[NH:12][CH:11]=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[C:29]([Cl:35])(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].N1C=CC=CC=1>C(Cl)(Cl)Cl>[ClH:35].[C:29]([O:1][CH:2]([CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([CH2:21][O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:19][CH2:20]1)[CH2:3][O:4][C:5]1[C:13]2[NH:12][CH:11]=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 178521376HCID 178521376, compound

Product 1

HCID 178447559HCID 178447559, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.8 g. 4-[2-Hydroxy-3-(4-phenoxymethylpiperidino)-propoxy]-benzimidazole and 1.3 g. pivaloyl chloride are boiled under reflux for 2 hours in 25 ml. pyridine. After stripping off the solvent, the residue is taken up in 100 ml. chloroform. The chloroform solution is thoroughly washed with water, dried over anhydrous sodium sulphate and finally mixed with 50 ml. ethereal hydrochloric acid. After evaporation and recrystallization from ethanol, there is obtained 4-[2-pivaloyloxy-3-(4-phenoxymethylpiperidino)-propoxy]-benzimidazole hydrochloride; m.p. 132°-134° C.

Workup

  1. temperatureunder reflux for 2 hours in 25 ml
  2. washThe chloroform solution is thoroughly washed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. additionfinally mixed with 50 ml
  5. customAfter evaporation and recrystallization from ethanol

Sources & evidence

ORD record
ord-507bf5e7439640a2bc45a4d406a6b4b5
Source dataset
uspto-grants-1979_03
Patent number
US04146630

Reaction notes

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