Sodium borohydride → HCID 23336385, compound

HRID 903550Notes

Reaction equation

HRID 903550 reaction equation
O[C:2]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][CH2:13][CH2:14][CH3:15])[C:4]2=[N:16][CH2:17][CH2:18][N:3]12.[BH4-].[Na+]>FC(F)(F)C(O)=O>[CH2:12]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]2[CH2:18][CH2:17][N:16]=[C:4]12)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23336408HCID 23336408, compound

Product 1

HCID 23336385HCID 23336385, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To 20 ml of trifluoroacetic acid were added portionwise with stirring both of 0.48 g of 5-hydroxy-10-(n-butyl)-5-phenyl-2,3,5,10-tetrahydroimidazo[2,1-b]quinazoline and 0.57 g of sodium borohydride below 0° C. under nitrogen. The reaction mixture was stirred at 0°-5° C. for 1 hour and the trifluoroacetic acid was evaporated under reduced pressure. To the residue were added 20 ml of ice-water and then 15 ml of 40% sodium hydroxide solution. After stirring for a while, the mixture was extracted with chloroform and the chloroform layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel using chloroform as an eluent to give 0.3 g of 10-(n-butyl)-5-phenyl-2,3,5,10-tetrahydroimidazo[2,1-b]quinazoline as a light yellow oil. An ethanol solution of the product was treated with ethanolic hydrogen chloride and evaporated under reduced pressure. The residue was recrystallized from ethanol to give colorless prisms (hydrochloride), m.p. 297° C. (decomp.).

Workup

  1. customthe trifluoroacetic acid was evaporated under reduced pressure
  2. additionTo the residue were added 20 ml of ice-water
  3. stirringAfter stirring for a while
  4. extractionthe mixture was extracted with chloroform
  5. washthe chloroform layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-56fdc58e64b44db9b89e29aa1b183e41
Source dataset
uspto-grants-1980_10
Patent number
US04228167

Reaction notes

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