Diketene → n-(2-(4,4-Diphenylpiperidin-1-yl)ethyl)acetoacetamide

HRID 396619Notes

Reaction equation

HRID 396619 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[NH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11]1>C1COCC1>[C:16]1([C:13]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][NH:7][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6])[CH2:15][CH2:14]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 230040551-(2-Aminoethyl)-4,4-diphenylpiperidine

Product 1

HCID 10690154n-(2-(4,4-Diphenylpiperidin-1-yl)ethyl)acetoacetamideYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diketene (1.50 mL, 19.2 mmol, 1.50 equiv) was added at 0° C. to a stirred solution of 1-(2-aminoethyl)-4,4-diphenylpiperidine (3.60 g, 12.8 mmol, 1.00 equiv) in anhydrous THF (40 mL) under argon, and stirring was continued at room temperature for 1 hour. The mixture was concentrated to give 4.10 g (88%) of white solid, which was characterized spectroscopically and used for the next reaction without purification.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-80eaf46b764b4fb7a5459a719a7ad8ba
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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