Acetic Acid → HCID 54129570, compound

HRID 582600Notes

Reaction equation

HRID 582600 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[O:28])[CH2:24][C:25](=[O:27])[CH3:26].C(O)(=O)C.N1CCCCC1>C(O)(C)C>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[O:28])[C:24](=[CH:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:25](=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 54398852HCID 54398852, compound

Product 1

HCID 54129570HCID 54129570, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4.7 g of 3-nitrobenzaldehyde and 9.5 g of 14-bromotetradecane-2-4-dione are dissolved in 100 ml isopropanol, 0.18 ml of acetic acid and 0.15 ml of piperidine are added and the mixture is stirred at RT for 4.5 days. It is cooled in an ice bath, and the crystallized product is filtered off with suction, washed with ice-cold isopropanol and dried. 10.5 g of the compound of m.p. 64-67° C. are obtained.

Workup

  1. temperatureIt is cooled in an ice bath
  2. filtrationthe crystallized product is filtered off with suction
  3. washwashed with ice-cold isopropanol
  4. customdried

Sources & evidence

ORD record
ord-d2a66f6561604f5b8499b5f27f38e34b
Source dataset
uspto-grants-1999_07
Patent number
US05925642

Reaction notes

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