Diketene → HCID 23004173, compound

HRID 396615Notes

Reaction equation

HRID 396615 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[OH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1>C1(C)C=CC=CC=1>[C:4]([O:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:16]1)(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 203693HCID 203693, compound

Product 1

HCID 23004173HCID 23004173, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diketene (0.95 mL, 12 mmol, 1.3 equiv) was added to a solution of 1-(3-hydroxypropyl)-4-phenylpiperidine (2.08 g, 9.48 mmol, 1.0 equiv) in toluene (30 mL), and the mixture was stirred under argon for 70 hours at room temperature. Removal of solvent gave 2.88 g (100%) of light brown, viscous oil, which was characterized spectroscopically and used for the next reaction without purification.

Workup

  1. customRemoval of solvent
  2. customgave 2.88 g (100%) of light brown
  3. customused for the next reaction without purification

Sources & evidence

ORD record
ord-0090d2b2dfa94cd8a2c4b459c27ea353
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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