Chlorosuccinimide → HCID 131728129, compound

HRID 2238674Notes

Reaction equation

HRID 2238674 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[Cl:24]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]2)=[C:12]([Cl:24])[CH:11]=1)[CH3:9])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86631938HCID 86631938, compound

Product 1

HCID 131728129HCID 131728129, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

80 mg of the t-butyl{(1S)-1-[4-(4-methylpiperazin-1-yl)phenyl]ethyl}carbamate [107-1] was dissolved in 3 mL of chloroform, then 70 mg of N-chlorosuccinimide was added thereto, and stirred at room temperature for 2 hours. The reaction solution was diluted with chloroform, washed with a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and thus obtained residue was purified by preparative thin-layer chromatography, to obtain 80 mg of t-butyl{(1S)-1-[3-chloro-4-(4-methylpiperazin-1-yl)phenyl]ethyl}carbamate [139-1] as a colorless oily product.

Workup

  1. washwashed with a saturated aqueous solution of sodium hydrogen carbonate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe insolubles were filtered
  4. concentrationthe filtrate was concentrated under reduced pressure, and thus obtained residue
  5. customwas purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-570ac99b13a048cbbddbbb3be1969415
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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