N-bromobutanimide → HCID 69417911, compound

HRID 853053Notes

Reaction equation

HRID 853053 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:24][CH:23]([CH3:25])[N:11]2[C:12]3[CH:13]=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:15]=[CH:16][C:17]=3[CH2:18][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:26]N1C(=O)CCC1=O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:24][C@@H:23]([CH3:25])[N:11]2[C:12]3[CH:13]=[C:14]([C:19]([F:20])([F:21])[F:22])[C:15]([Br:26])=[CH:16][C:17]=3[CH2:18][C@@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69416466HCID 69416466, compound

Product 1

HCID 69417911HCID 69417911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methyl-7-trifluoromethyl-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester (0.83 g; 2.4 mmol) was dissolved in dimethylformamide (7 mL) and N-bromosuccinimide (0.43 g, 2.5 mmol) was added in portions. The mixture was stirred for 1 h, added to ice water (500 mL) and extracted with diethylether (2×150 mL). Organic phases were pooled, washed with water, dried with MgSO4 and the solvent was removed in vacuo. Chromatography on silica gel (n-hexane/diethylether 4:1) yielded the title product as a colorless wax (0.99 g, 98%). ISP-MS: m/e=435.3, 437.3 (M+H+).

Workup

  1. extractionextracted with diethylether (2×150 mL)
  2. washwashed with water
  3. dry with materialdried with MgSO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a551e06f73f6471db2a4ef16f4c9a9c1
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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