Diketene → n-(3-(4-Phenylpiperidin-1-yl)propyl)acetoacetamide

HRID 382667Notes

Reaction equation

HRID 382667 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[NH2:7][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>C1COCC1>[C:17]1([CH:14]2[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6])[CH2:16][CH2:15]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 22725156HCID 22725156, compound

Product 1

HCID 10542422n-(3-(4-Phenylpiperidin-1-yl)propyl)acetoacetamideYield 104.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diketene (1.64 mL, 21.3 mmol, 1.50 equiv) was added at 0° C. to a stirred solution of 1-(3-aminopropyl)-4-phenylpiperidine (3.10 g, 14.2 mmol, 1.00 equiv) in anhydrous THF (30 mL) under argon, and stirring was continued at room temperature for 1 hour. The mixture was concentrated to give 4.50 g (100%) of viscous orange oil, which was characterized spectroscopically and used for the next reaction without purification.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-814cb26c40c84631ac293a5875a7fbfe
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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