Sulfuric Acid → (r)-1-Benzoylnipecotamide

Reaction equation

S(=O)(=O)(O)O.[NH:6]1[CH2:14][CH2:13][CH2:12][CH:8]([C:9]([NH2:11])=[O:10])[CH2:7]1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>>[C:15]([N:6]1[CH2:14][CH2:13][CH2:12][C@@H:8]([C:9]([NH2:11])=[O:10])[CH2:7]1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 7412Benzoyl chloride

HCID 14798Sodium Hydroxide

HCID 929803-Piperidinecarboxamide

Product 1

HCID 59294610(r)-1-BenzoylnipecotamideYield 88%

Conditions

Temperature: 15 °C

Procedure

Concentrated sulfuric acid is added to the reaction mixture obtained in Example 4 (amount: 10 g, net weight of (R)-nipecotamide: 1 g) to adjust the pH to 9. Benzoyl chloride (3.5 g, 2.5 equivalents) was slowly added dropwise, and the pH of the reaction mixture was kept from 7 to 9 by a 30% aqueous sodium hydroxide solution. After completion of the dropwise addition, the solution was stirred at 15° C. for 3 hours to obtain a solution containing the title compound (1.6 g, yield: 88%).