1-Chloroethyl chloroformate → HCID 57868006, compound

HRID 425995Notes

Reaction equation

HRID 425995 reaction equation
ClC(OC(Cl)C)=O.C([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]2[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:23]=2[C:24]([NH:26][C:27]2[CH:36]=[C:35]3[C:30]([CH2:31][CH2:32][C:33](=[O:38])[N:34]3[CH3:37])=[CH:29][CH:28]=2)=[O:25])[CH2:17][CH2:16]1)C1C=CC=CC=1>ClCCCl>[Cl:43][C:41]1[CH:40]=[CH:39][C:23]([C:24]([NH:26][C:27]2[CH:36]=[C:35]3[C:30]([CH2:31][CH2:32][C:33](=[O:38])[N:34]3[CH3:37])=[CH:29][CH:28]=2)=[O:25])=[C:22]([NH:21][CH:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)[CH:42]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 66703594HCID 66703594, compound

Product 1

HCID 57868006HCID 57868006, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Under ice-cooling, 1-chloroethyl chloroformate was added to a 1,2-dichloroethane solution of 2-[(1-benzylpiperidin-4-yl)amino]-4-chloro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)benzamide. This was stirred for 1 hour under heat reflux and then concentrated under a reduced pressure. After dissolving in methanol, this was stirred for 2 hours under heat reflux. After concentration of the reaction liquid under a reduced pressure, the residue was purified by silica gel column chromatography to obtain 4-chloro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-(piperidin-4-ylamino)benzamide.

Workup

  1. temperatureUnder ice-cooling
  2. temperatureunder heat
  3. temperaturereflux
  4. concentrationconcentrated under a reduced pressure
  5. dissolutionAfter dissolving in methanol
  6. stirringthis was stirred for 2 hours
  7. temperatureunder heat
  8. temperaturereflux
  9. customAfter concentration of the reaction liquid under a reduced pressure
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-852d8954849f4f4d84ceb2bc9e542dc8
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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