Hydrochloric Acid → 1-(4-chlorophenyl)-2-(3,4-dihydropyrimido[1,2-a]benzimidazol-10(2H)-yl)ethanol

HRID 1683729Notes

Reaction equation

HRID 1683729 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:25]=[CH:24][C:7]([C:8](=[O:23])[CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]3[CH2:19][CH2:20][CH2:21][N:22]=[C:11]23)=[CH:6][CH:5]=1.Cl>C(O)C>[OH:23][CH:8]([C:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:25][CH:24]=1)[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]2[CH2:19][CH2:20][CH2:21][N:22]=[C:11]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 791782HCID 791782, compoundHCID 4311764Sodium borohydride

Product 1

HCID 28997651-(4-chlorophenyl)-2-(3,4-dihydropyrimido[1,2-a]benzimidazol-10(2H)-yl)ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add 0.35 g (9.3 mmol) of sodium borohydride in small portions, with vigorous stirring, to a suspension of 3.0 g (9.3 mmol) of 10-(4-chlorophenacyl)-2,3,4,10-tetrahydropyrimidino[1,2-a]benzimidazole (obtained in Example 50) in 20 ml of ethanol. Maintain stirring for one hour and leave for 12 hours at room temperature. Acidify with hydrochloric acid, and evaporate the reaction mixture. Treat the residue with ammonium hydroxide and extract with chloroform. The organic phase obtained is passed over a column of alumina. Evaporate the solvent. The residue is the title compound.

Workup

  1. temperatureMaintain
  2. customleave for 12 hours at room temperature
  3. customevaporate the reaction mixture
  4. additionTreat the residue with ammonium hydroxide
  5. extractionextract with chloroform
  6. customThe organic phase obtained
  7. customEvaporate the solvent

Sources & evidence

ORD record
ord-1cbd5d10e6604fc8bd394ae2639bf8b0
Source dataset
uspto-grants-1997_06
Patent number
US05639756

Reaction notes

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