Diketene → HCID 53902317, compound

HRID 973707Notes

Reaction equation

HRID 973707 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[OH: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>CC(C)=O.C(Cl)Cl>[C:4]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][C:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:15][CH2:14]1)(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

5

Reactant 2

HCID 12661DiketeneHCID 19988807N-[2-(2-Hydroxyethoxy)-ethyl]-4,4-diphenylpiperidine

Product 1

HCID 53902317HCID 53902317, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

20 ml of a 50% strength solution of diketene in acetone are added dropwise to 32.5 g of N-[2-(2-hydroxyethoxy)-ethyl]-4,4-diphenylpiperidine and about 0.1 g of N,N-dimethylaminopyridine in 200 ml of methylene chloride at the boiling point, with vigorous stirring. After boiling under reflux for 1 h, the solution is allowed to cool and is concentrated to constant weight under a high vacuum. The pale yellow viscous coil which remains is used for the next stage without further purification.

Workup

  1. temperatureunder reflux for 1 h
  2. temperatureto cool
  3. concentrationis concentrated to constant weight under a high vacuum
  4. customThe pale yellow viscous coil which remains is used for the next stage without further purification

Sources & evidence

ORD record
ord-d9980ea9e58e4315a93008385f6c40f4
Source dataset
uspto-grants-1991_11
Patent number
US05064839

Reaction notes

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