Borane → HCID 19087663, compound

HRID 1464285Notes

Reaction equation

HRID 1464285 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16](=O)[CH2:17][CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23](=[O:30])[NH:22][C:21]2=[O:31])[CH2:12][CH2:11]1)([O-:3])=[O:2].B>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23](=[O:30])[NH:22][C:21]2=[O:31])[CH2:12][CH2:11]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6331BoraneHCID 19087662HCID 19087662, compound

Product 1

HCID 19087663HCID 19087663, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1-[4-{4-(2-nitrophenyl)piperazin-1-yl}-4-oxo-butyl]-2,4(1H,3H)-quinazolinedione (500 mg) in tetrahydrofuran (10 ml) was added 1M borane in tetrahydrofuran (3.42 ml) on an ice-bath. After refluxing for 30 minutes, the reaction mixture was quenched with 1N hydrochloric acid (7 ml), and refluxed for additional 30 minutes. The mixture was made alkaline with saturated aqueous sodium bicarbonate, diluted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated. The obtained residue was chromatographed on silica gel (20 g) eluting with chloroform-methanol (20:1 V/V) to give crystals. Recrystallization from ethanol gave 1-[4-{4-(2-nitrophenyl)piperazin-1-yl}butyl]-2,4(1H,3H)-quinazolinedione (77 mg).

Workup

  1. temperatureAfter refluxing for 30 minutes
  2. customthe reaction mixture was quenched with 1N hydrochloric acid (7 ml)
  3. temperaturerefluxed for additional 30 minutes
  4. additiondiluted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium bicarbonate and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe obtained residue was chromatographed on silica gel (20 g)
  9. washeluting with chloroform-methanol (20:1 V/V)
  10. customto give crystals
  11. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-e467c558f79f4032acb5895d831ff925
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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