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

HRID 1603735Notes

Reaction equation

HRID 1603735 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-9ba1354ae04c41b08033be4bd5850dd7
Source dataset
uspto-grants-1999_11
Patent number
US05990128

Reaction notes

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