Acetonitrile → HCID 86649005, compound

HRID 518084Notes

Reaction equation

HRID 518084 reaction equation
[CH3:1][N:2]([CH:21]([CH3:23])[CH3:22])[C:3]1[CH:20]=[N:19][C:6]2[CH2:7][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH2:10][O:11][C:5]=2[N:4]=1.[Br:24]N1C(=O)CCC1=O.C(#N)C>O>[Br:24][C:20]1[C:3]([N:2]([CH3:1])[CH:21]([CH3:23])[CH3:22])=[N:4][C:5]2[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:7][C:6]=2[N:19]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 66994124HCID 66994124, compound

Product 1

HCID 86649005HCID 86649005, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of tert-butyl 3-[methyl(1-methylethyl)amino]-6,7-dihydropyrazino[2,3-f][1,4]oxazepine-8(9H)-carboxylate (1.0 g), N-bromosuccinimide (608 mg) and acetonitrile (20 mL) was stirred at room temperature for 16 hr. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient: 3-*30% ethyl acetate/hexane) to give the title compound (915 mg, 74%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient: 3-*30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3a6c5e185d3c452ea6a144eceaff2d25
Source dataset
uspto-grants-2015_08
Patent number
US09115139B2

Reaction notes

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