Sulfuric Acid → (3R)-1-Benzoyl-3-piperidinecarboxamide

HRID 2195605Notes

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(3R)-1-Benzoyl-3-piperidinecarboxamideYield 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%).

Workup

additionAfter completion of the dropwise addition
customto obtain a solution

Sources & evidence

ORD record: ord-7b54f604e9a44056bc0ccefe0ab531c0
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338142B2

Reaction notes

Loading…