N-bromobutanimide → HCID 86683748, compound

HRID 519359Notes

Reaction equation

HRID 519359 reaction equation
[C:1]1(=[O:14])[C:6]2=[CH:7][C:8]3[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=3[N:5]2[CH2:4][CH2:3][NH:2]1.[Br:15]N1C(=O)CCC1=O>CN(C)C=O.O>[Br:15][C:7]1[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[N:5]2[CH2:4][CH2:3][NH:2][C:1](=[O:14])[C:6]=12

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 580439603,4,6,7,8,9-Hexahydropyrazino[1,2-a]indol-1(2H)-one

Product 1

HCID 86683748HCID 86683748, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Into a 250-mL 3-necked round-bottom flask was placed a solution of 1H,2H,3H,4H,6H,7H,8H,9H-pyrazino[1,2-a]indol-1-one 104j (9.5 g, 49.94 mmol, 1.00 equiv) in N,N-dimethylformamide (100 mL), followed by the addition of N-bromosuccinimide (9.8 g, 55.06 mmol, 1.10 equiv) in several batches at 0° C. The resulting solution was stirred at room temperature for 2 h and diluted with 500 mL of water. The precipitate was filtered and dried in a vacuum oven to afford 9.5 g (71%) of 119a as a light brown solid.

Workup

  1. customInto a 250-mL 3-necked round-bottom flask was placed
  2. filtrationThe precipitate was filtered
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-27945daad25e465b9b5cf4efad965f3c
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

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