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

HRID 382679Notes

Reaction equation

HRID 382679 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-59f1c0f315a742f8841bf03f03c37700
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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