Water → HCID 22660612, compound

HRID 392754Notes

Reaction equation

HRID 392754 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)=[O:11].[Br:19]Br.O.[OH-].[Na+]>C(O)(=O)C>[Br:19][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]=1[C:10]([N:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 4060730(1H-indol-2-yl)(4-methylpiperazin-1-yl)methanone

Product 1

HCID 22660612HCID 22660612, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(1H-Indol-2-yl)-(4-methyl-piperazin-1-yl)-methanone (Example 4, 0.222 g) in acetic acid (1 mL) at ambient temperature was treated with bromine (0.05 mL) and stirred for 7 h. The reaction mixture was poured into water and adjusted to basic pH by addition of 1 M sodium hydroxide. The mixture was extracted with dichloromethane. The organic extracts were combined, dried over sodium sulfate, filtered, and concentrated to give crude product. Purification via silica gel chromatography, eluting with 1-8% methanol/dichloromethane, afforded the title compound (0.154 g).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product
  6. customPurification via silica gel chromatography
  7. washeluting with 1-8% methanol/dichloromethane

Sources & evidence

ORD record
ord-b74a3a7cb68343d18395e14ea718ba9b
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

Loading…