Bromine → HCID 69414214, compound

HRID 853070Notes

Reaction equation

HRID 853070 reaction equation
[Br:1]Br.[CH2:3]([C:5]1[C:13]2[N:12]3[C@H:14]([CH3:18])[CH2:15][NH:16][CH2:17][C@H:11]3[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)[CH3:4].C([O-])(=O)C.[Na+]>C(O)(=O)C.ClCCl>[Br:1][C:7]1[CH:6]=[C:5]([CH2:3][CH3:4])[C:13]2[N:12]3[C@H:14]([CH3:18])[CH2:15][NH:16][CH2:17][C@H:11]3[CH2:10][C:9]=2[CH:8]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 45095244HCID 45095244, compound

Product 1

HCID 69414214HCID 69414214, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Bromine (0.2 M solution in acetic acid, 0.48 mL, 96 μmol) was added dropwise at room temperature to a solution of (4R,10aR)-6-ethyl-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole (21 mg, 97 mol) and sodium acetate (8.0 mg, 97 μmol) in acetic acid (0.5 mL). After 30 min the reaction mixture was diluted with dichloromethane and extracted with 2 M aq. potassium hydroxide solution, dried (MgSO4), and evaporated. Chromatography on SiO2 (CH2Cl2/MeOH/NH4OH 95:5:0.1) yielded the title compound (9 mg, 31%). Yellow oil. ISP-MS: m/e=295.3, 297.3 ([M+H]+).

Workup

  1. extractionextracted with 2 M aq. potassium hydroxide solution
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-566ea91ca5bb473aaf9bf91d3aaf52c3
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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