Sulfuric Acid → HCID 59294624, compound

HRID 2195606Notes

Reaction equation

HRID 2195606 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.[CH3:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.[OH-].[Na+]>>[CH3:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:6]2[CH2:14][CH2:13][CH2:12][C@@H:8]([C:9]([NH2:11])=[O:10])[CH2:7]2)=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 134054-Methylbenzoyl ChlorideHCID 14798Sodium HydroxideHCID 929803-Piperidinecarboxamide

Product 1

HCID 59294624HCID 59294624, compoundYield 34.5%

Conditions

Temperature
15 °C

Procedure

Concentrated sulfuric acid is added to the reaction mixture obtained in Example 4 (amount: 30 g, net weight of (R)-nipecotamide: 3 g) to adjust the pH to 9. To the mixture, p-Methylbenzoyl chloride (8.0 g, 2.2 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 and the precipitated crystal was filtered off. The crystal was dried under reduced pressure to obtain the title compound as white crystal (4.4 g, yield: 760).

Workup

  1. additionAfter completion of the dropwise addition
  2. filtrationthe precipitated crystal was filtered off
  3. customThe crystal was dried under reduced pressure

Sources & evidence

ORD record
ord-3dfe8877735943a38dd7655a65a3fa2f
Source dataset
uspto-grants-2012_12
Patent number
US08338142B2

Reaction notes

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