Benzene → HCID 20570825, compound

HRID 1577519Notes

Reaction equation

HRID 1577519 reaction equation
[ClH:1].[OH:2][CH:3]([CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH2:19][CH2:18]1)[CH2:4][O:5][C:6]1[C:14]2[NH:13][CH:12]=[N:11][C:10]=2[C:9]([CH3:15])=[CH:8][CH:7]=1.[C:31](O)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(OC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C=CC=CC=1>CN(C)C=O>[ClH:1].[C:31]([O:2][CH:3]([CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH2:19][CH2:18]1)[CH2:4][O:5][C:6]1[C:14]2[NH:13][CH:12]=[N:11][C:10]=2[C:9]([CH3:15])=[CH:8][CH:7]=1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 243Benzoic AcidHCID 7167Benzoic anhydrideHCID 20570865HCID 20570865, compound

Product 1

HCID 20570825HCID 20570825, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.87 g. 4-{2-Hydroxy-3-[4-(2-pyridyloxymethyl)-piperidino]-propoxy}-7-methylbenzimidazole (preparation see Example 13), 19.5 g. benzoic acid and 2.12 g. benzoic anhydride are heated under reflux for 2 hours in 100 ml. benzene and 25 ml. dimethylformamide. After removing the solvent, the residue is taken up in 100 ml. water, rendered alkaline with concentrated aqueous ammonia solution and extracted with chloroform. The chloroform phase is washed with water, dried over anhydrous sodium sulphate and evaporated. The residue is taken up in ethanol and mixed with ethereal hydrochloric acid. After adding isopropanol and diethyl ether, there crystallize out 2.1 g. (41% of theory) 4-{2-benzoyloxy-3-[4-(2-pyridyloxymethyl)-piperidino]-propoxy}-7-methylbenzimidazole hydrochloride; m.p. 178°-181° C.

Workup

  1. temperatureunder reflux for 2 hours in 100 ml
  2. customAfter removing the solvent
  3. extractionextracted with chloroform
  4. washThe chloroform phase is washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. additionmixed with ethereal hydrochloric acid
  8. additionAfter adding isopropanol and diethyl ether, there
  9. customcrystallize out 2.1 g

Sources & evidence

ORD record
ord-b6ae42428bdc463abfa67abe489a6d8f
Source dataset
uspto-grants-1981_09
Patent number
US04288442

Reaction notes

Loading…