Acetic Acid → HCID 19031118, compound

HRID 266785Notes

Reaction equation

HRID 266785 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH:21]=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:31]CC)(=O)[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:28]([O:27][C:25]([C:24]1[C:23](=[O:31])[N:14]([CH:11]2[CH2:10][CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][CH2:12]2)[C:15]2[C:16]([CH:21]=1)=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:26])[CH3:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 19030736HCID 19030736, compound

Product 1

HCID 19031118HCID 19031118, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-(1-benzyl-4-piperidinyl)-o-formylaniline (32.0 g), diethyl malonate (35.4 g), piperidine (5 ml), acetic acid (2.5 ml), anhydrous toluene (320 ml) and molecular sieves (32 g) is refluxed for 8 hours. After concentrating the reaction mixture, dichloromethane is added to the residue and the mixture is filtered. Water is added to the filtrate and the mixture is extracted with dichloromethane. After concentrating the extract, the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane/methanol=50/1) to give 3-ethoxycarbonyl-1-(1-benzyl-4-piperidinyl)carbostyril (27.2 g).

Workup

  1. temperatureis refluxed for 8 hours
  2. concentrationAfter concentrating the reaction mixture, dichloromethane
  3. additionis added to the residue
  4. filtrationthe mixture is filtered
  5. additionWater is added to the filtrate
  6. extractionthe mixture is extracted with dichloromethane
  7. concentrationAfter concentrating the extract
  8. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane/methanol=50/1)

Sources & evidence

ORD record
ord-b8e9999e1d1048449551800a13e8c1ce
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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