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

HRID 322126Notes

Reaction equation

HRID 322126 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:13]1>C1COCC1>[C:18]1([C:15]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6])[CH2:17][CH2:16]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 230041441-(4-Aminobutyl)-4,4-diphenylpiperidine

Product 1

HCID 10596702n-(4-(4,4-Diphenylpiperidin-1-yl)butyl)acetoacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diketene (1.68 mL, 21.9 mmol, 1.50 equiv) was added at 0° C. to a stirred solution of 1-(4-aminobutyl)-4,4-diphenylpiperidine (4.50 g, 14.6 mmol, 1.00 equiv) in anhydrous THF (40 mL) under argon, and stirring was continued at room temperature for 1.5 hours. The mixture was concentrated and the residual oil washed with hexane (3×50 mL) to give 5.17 g (90%) of light yellow oil, which was characterized spectroscopically and used for the next reaction without purification.

Workup

  1. concentrationThe mixture was concentrated
  2. washthe residual oil washed with hexane (3×50 mL)
  3. customto give 5.17 g (90%) of light yellow oil, which
  4. customused for the next reaction without purification

Sources & evidence

ORD record
ord-ed18cbe121cb4f00b5f0e7f0b0ed2753
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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