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

HRID 396622Notes

Reaction equation

HRID 396622 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-ad621fca3bae41bda0f3213ef084b855
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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