Acetic Acid → HCID 69587893, compound

HRID 1791121Notes

Reaction equation

HRID 1791121 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[O:11]=[C:12]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)[CH2:13][C:14]([O:16][CH3:17])=[O:15].N1CCCCC1.C(O)(=O)C>C(O)(C)C>[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[C:13]([C:12](=[O:11])[CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=1)[C:14]([O:16][CH3:17])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 15547737HCID 15547737, compound

Product 1

HCID 69587893HCID 69587893, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2.44 g (15.4 mmol) of 2-chloro-4-fluorobenzaldehyde and 3.19 g (15.4 mmol) of the compound from Example X in 20 ml of isopropanol are mixed with 0.1 ml of piperidine and 0.13 ml of glacial acetic acid. Stirring at room temperature overnight is followed by concentration, and the residue is chromatographed on silica gel with dichloromethane->dichloromethane/methanol (50:1) as mobile phase. The product is employed further as cis/trans mixture.

Workup

  1. concentrationis followed by concentration
  2. customthe residue is chromatographed on silica gel with dichloromethane->dichloromethane/methanol (50:1) as mobile phase

Sources & evidence

ORD record
ord-d29d70ea4abd46d3b4624c631e1e26d1
Source dataset
uspto-grants-2006_07
Patent number
US07074784B2

Reaction notes

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