Toluene → Benzoylpiperidine

HRID 430834Notes

Reaction equation

HRID 430834 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[OH-].[Na+].C1(C)C=CC=CC=1>O>[C:1]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7412Benzoyl chlorideHCID 8082PiperidineHCID 14798Sodium Hydroxide

Product 1

HCID 69892BenzoylpiperidineYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzoyl chloride (500 mL, 606 g, 4.3 mol) was added dropwise to a rapidly stirring mixture of piperidine (426 mL, 367 g, 4.3 mol), sodium hydroxide (190 g, 4.7 mol, 1.1 equivalents), toluene (1 L), and water (1.7 L) over a period of 70 minutes. After the addition was complete, the mixture was stirred at 25° C. for one hour. The organic and aqueous phases were separated, and the organic phase was washed with 2N hydrochloric acid (2×100 mL), concentrated by rotary evaporation, and distilled under vacuum to yield benzoylpiperidine as a colorless liquid which crystallized on standing. (779 g, 95% yield, bp 169° C. to 171° C.).

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at 25° C. for one hour
  3. customThe organic and aqueous phases were separated
  4. washthe organic phase was washed with 2N hydrochloric acid (2×100 mL)
  5. concentrationconcentrated by rotary evaporation
  6. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-566653566fe44a43909f2571ba4da775
Source dataset
uspto-grants-2001_11
Patent number
US06323344B1

Reaction notes

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