N-bromobutanimide → 9-Bromo-1,2,3,4,4a,5-hexahydropyrazino[1,2-a][1,5]benzodiazepin-6(7h)-one

HRID 1035276Notes

Reaction equation

HRID 1035276 reaction equation
[CH2:1]1[N:6]2[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[NH:9][C:10](=[O:12])[CH2:11][CH:5]2[CH2:4][NH:3][CH2:2]1.[Br:17]N1C(=O)CCC1=O>C(O)(=O)C.O>[Br:17][C:14]1[CH:15]=[CH:16][C:7]2[N:6]3[CH2:1][CH2:2][NH:3][CH2:4][CH:5]3[CH2:11][C:10](=[O:12])[NH:9][C:8]=2[CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 497641661,2,3,4,4a,5-Hexahydropyrazino[1,2-a][1,5]benzodiazepin-6(7h)-one

Product 1

HCID 497645439-Bromo-1,2,3,4,4a,5-hexahydropyrazino[1,2-a][1,5]benzodiazepin-6(7h)-one

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

To a solution of Example 1D (1.54 g, 6.07 mmol) in acetic acid/water (1:1, 20 mL) was added N-bromosuccinimide (1.08 g, 6.07 mmol). The reaction mixture was stirred at room temperature for 2 hours. Product precipitated. The precipitate was collected to afford the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 7.36 (d, J=8.54 Hz, 1H), 7.16 (s, 1H), 7.11 (d, J=8.85 Hz, 1H), 3.54-3.63 (m, 1H), 3.22-3.40 (m, 4H), 2.93-3.07 (m, 2H), 2.65-2.72 (m, 1H), 2.08 (d, J=13.73 Hz, 1H); MS (ESI) m/z 297.8 (M+H)+.

Workup

  1. customProduct precipitated
  2. customThe precipitate was collected

Sources & evidence

ORD record
ord-c8dc6f67688946df9706ebc48db2b0e0
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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