Water → HCID 66688781, compound

HRID 1500613Notes

Reaction equation

HRID 1500613 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:7][N:8]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:9][CH2:10][C:11]=1[NH2:12])=[O:5])[CH3:2].N1C=CC=CC=1.[C:28](Cl)(=[O:36])[O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH2:7][N:8]([C:13](=[O:21])[C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH2:9][CH2:10][C:11]=1[NH:12][C:28]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:36])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 66685847HCID 66685847, compound

Product 1

HCID 66688781HCID 66688781, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl-4-amino-1-(4-chlorobenzoyl)-1,2,5,6-tetrahydropyridine-3-carboxylate (7.0 g) was dissolved in methylene chloride (140 ml), pyridine (6.0 ml) and phenyl chlorocarbonate (6.0 ml) were added under ice cooling, and the resultant mixture was stirred at room temperature for 2 hours. To the reaction solution, water was added and the mixture was extracted with methylene chloride. After the organic layer was washed with citric acid solution and a saturated saline solution, the organic layer was dried over sodium sulfate, filtrated and concentrated. The resultant residue was subjected to medium-pressure column fractionation (solvent; ethyl acetate:hexane=20:80 to 60:40). The titled compound (8.35 g) was obtained as a white powder.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washAfter the organic layer was washed with citric acid solution
  3. dry with materiala saturated saline solution, the organic layer was dried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8dc10142443f43ac8ed7ab1786f7cb9f
Source dataset
uspto-grants-2015_12
Patent number
US09206173B2

Reaction notes

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