Propanal → HCID 57786122, compound

HRID 1628653Notes

Reaction equation

HRID 1628653 reaction equation
Br[C:2]1[C:7]2[N:8]3[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=4[Cl:23])[C:9]3=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH:29](=[O:32])[CH2:30][CH3:31]>O1CCCC1.[Cl-].[NH4+]>[Cl:23][C:17]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=1[N:11]1[C:9]2=[N:10][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH:29]([OH:32])[CH2:30][CH3:31])[C:7]=3[N:8]2[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 527PropanalHCID 57786070HCID 57786070, compoundHCID 178418339Butyllithium

Product 1

HCID 57786122HCID 57786122, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 7-bromo-1-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole (570 mg, 1.39 mmol) in tetrahydrofuran (10 mL) was added n-butyllithium (1.60 M solution in n-hexane, 0.97 mL, 1.55 mmol) at −78° C., and the mixture was stirred for 10 min. To the mixture was added propionaldehyde (0.30 mL, 4.16 mmol), and the mixture was stirred at −78° C. for 10 min, at 0° C. for 3 hr. The mixture was diluted with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 5-25% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate to give the title compound as a colorless crystal (101 mg, 0.259 mmol, 19%).

Workup

  1. stirringthe mixture was stirred at −78° C. for 10 min, at 0° C. for 3 hr
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 5-25% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give the solid, which
  10. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0dd3498af86e42d08a0585580d8444a4
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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