Acetic Acid → 2-[2-(4,4-Diphenylpiperid-1-yl)-ethoxy]-ethyl 2-acetyl-3-(3-nitrophenyl)-acrylate

HRID 973706Notes

Reaction equation

HRID 973706 reaction equation
[C:1]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[N+:31]([C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH:37]=O)([O-:33])=[O:32].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1.C1C=CC=CC=1.O>[C:3]([C:2](=[CH:37][C:36]1[CH:39]=[CH:40][CH:41]=[C:34]([N+:31]([O-:33])=[O:32])[CH:35]=1)[C:1]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:15][CH2:14]1)=[O:6])(=[O:4])[CH3:5]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 53902317HCID 53902317, compound

Product 1

HCID 537545682-[2-(4,4-Diphenylpiperid-1-yl)-ethoxy]-ethyl 2-acetyl-3-(3-nitrophenyl)-acrylate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4.1 g of 2-[2-(4,4-diphenylpiperid-1-yl)-ethoxy]-ethyl acetoacetate, 15 g of 3-nitrobenzaldehyde, 8 ml of acetic acid and 0.5 ml of piperidine are heated at the boiling point in 300 ml of toluene using a water separator. After 1.9 ml of water have been separated off, the cooled solution is washed with saturated sodium bicarbonate solution and then with water. After the organic phase has been dried with sodium sulfate, the clear reddish-brown solution is concentrated under a high vacuum. The resulting viscous residue is used for the condensation reaction, without further purification. Yield: 53 g of crude product as a cis/trans-isomer mixture. Other entraining agents which are suitable are: benzene and chlorinated hydrocarbons. The yield of crude product is 95-100% of theory.

Workup

  1. customAfter 1.9 ml of water have been separated off
  2. washthe cooled solution is washed with saturated sodium bicarbonate solution
  3. dry with materialAfter the organic phase has been dried with sodium sulfate
  4. concentrationthe clear reddish-brown solution is concentrated under a high vacuum
  5. customThe resulting viscous residue is used for the condensation reaction, without further purification

Sources & evidence

ORD record
ord-37de7d50b59c4ec7b1a819d1d1587e7b
Source dataset
uspto-grants-1991_11
Patent number
US05064839

Reaction notes

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