Chlorosuccinimide → HCID 22660587, compound

HRID 392758Notes

Reaction equation

HRID 392758 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].[Cl:19]N1C(=O)CCC1=O>ClCCl.CCOCC>[Cl: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

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 4060730(1H-indol-2-yl)(4-methylpiperazin-1-yl)methanone

Product 1

HCID 22660587HCID 22660587, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

(1H-Indol-2-yl)-(4-methyl-piperazin-1-yl)-methanone (Example 4, 0.5 g) in dichloromethane (3 mL) at ambient temperature was treated with N-chlorosuccinimide (0.301 g) and stirred for 6 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 (0.36 g). 1H NMR (400 MHz, CDCl3): δ 2.36 (3H), 2.52 (4H), 3.79 (4H), 7.21 (1H), 7.31 (1H), 7.38 (1H), 7.64 (1H), 9.05 (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-892290a4abcf4e039085ce70eb2efdba
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

Loading…