Hydrochloric Acid → 8,9-dihydro-7-[(hydroxy)(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one hydrochloride

HRID 847499Notes

Reaction equation

HRID 847499 reaction equation
[OH:1][CH:2]([C:17]1[N:18]=[CH:19][N:20](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:21]=1[CH3:22])[CH:3]1[C:15](=[O:16])[N:7]2[C:8]3[C:13]([CH:14]=[C:6]2[CH2:5][CH2:4]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[ClH:42]>C(O)(=O)C.O.C(OCC)(=O)C.CCOCC>[ClH:42].[OH:1][CH:2]([C:17]1[N:18]=[CH:19][NH:20][C:21]=1[CH3:22])[CH:3]1[C:15](=[O:16])[N:7]2[C:8]3[C:13]([CH:14]=[C:6]2[CH2:5][CH2:4]1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 117569938,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one

Product 1

HCID 190973268,9-dihydro-7-[(hydroxy)(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one hydrochloride

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of 8,9-dihydro-7-[(hydroxy)-(5-methyl-1-trityl-1H-imidazol-4-vl-)methyl]pyrido[1,2-a]-indol-6(7H)-one (1.1 g) in acetic acid-water (3:1, 48 ml) was stirred at 65° C. for 90 minutes. After evaporation of the solvent, the residue was diluted with water, neutralized with an aqueous solution of sodium hydrogencarbonate, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The obtained amorphous powder contained two products which showed close Rf values (0.3 and 0.4 respectively) by TLC (20% methanol-chloroform). Separation with silica gel column chromatography (10% methanol-chloroform) gave two fractions. The residue obtained from the first eluted fraction was dissolved in ethyl acetate and treated with hydrogen chloride in ether to give one isomer with an upper Rf value of 8,9-dihydro-7-[(hydroxy)(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one hydrochloride (86.1 mg), which was designated as the isomer A.

Workup

  1. customAfter evaporation of the solvent
  2. additionthe residue was diluted with water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customshowed close Rf values (0.3 and 0.4 respectively) by TLC (20% methanol-chloroform)
  8. customSeparation with silica gel column chromatography (10% methanol-chloroform)
  9. customgave two fractions
  10. customThe residue obtained from the first eluted fraction

Sources & evidence

ORD record
ord-252fd04d0b534d6da6fc15cf2c0d7fdb
Source dataset
uspto-grants-1992_08
Patent number
US05141945

Reaction notes

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