Diketene → 3-(4,4-Diphenylpiperid-1-yl)-propyl acetoacetate

HRID 850001Notes

Reaction equation

HRID 850001 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][OH:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]=[C:24]1[O:28][C:26](=[O:27])[CH2:25]1>C1(C)C=CC=CC=1.CC(C)=O>[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][O:16][C:26](=[O:27])[CH2:25][C:24]([CH3:23])=[O:28])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 12661DiketeneHCID 104022594,4-Diphenyl-1-piperidinepropanol

Product 1

HCID 99770173-(4,4-Diphenylpiperid-1-yl)-propyl acetoacetate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

23.6 g of 3-(4,4-diphenylpiperid-1-yl)-propanol were dissolved in 100 ml of absolute toluene, and 16 ml of a 50% strength solution of diketene in acetone were added with stirring. After standing for several days at room temperature (monitored by thin layer chromatography), the mixture was concentrated, and the residue was dried under high vacuum. The pale yellow, viscous oil which remains was employed without further purification for the next stage.

Workup

  1. waitAfter standing for several days at room temperature
  2. concentration(monitored by thin layer chromatography), the mixture was concentrated
  3. customthe residue was dried under high vacuum
  4. customThe pale yellow, viscous oil which remains was employed without further purification for the next stage

Sources & evidence

ORD record
ord-b7e3a9d160e843df8696c3ebc33e81ea
Source dataset
uspto-grants-2000_01
Patent number
US06015819

Reaction notes

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