Chlorosuccinimide → HCID 22660613, compound

HRID 392760Notes

Reaction equation

HRID 392760 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[CH:5]2.[Cl:20]N1C(=O)CCC1=O>ClCCl.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[C:5]2[Cl:20]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 9923162HCID 9923162, compound

Product 1

HCID 22660613HCID 22660613, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

(5-Bromo-1H-indol-2-yl)-(4-methyl-piperazin-1-yl)-methanone (Example 3, 0.27 g) in dichloromethane (3 mL) at ambient temperature was treated with N-chlorosuccinimide (0.103 g) and stirred for 18 h. The reaction mixture was diluted with ether, washed with water, saturated sodium hydrogencarbonate solution and then brine, 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 (0.16 g). 1H NMR (400 MHz, CDCl3): δ 2.35 (3H), 2.52 (4H), 3.78 (4H), 7.23 (1H), 7.35 (1H), 7.74 (1H), 9.84 (1H).

Workup

  1. washwashed with water, saturated sodium hydrogencarbonate solution
  2. dry with materialbrine, dried 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-796e5a6ef8934ec3a34abe2df785327e
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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