Sulfuric Acid → HCID 22993440, compound

HRID 1275241Notes

Reaction equation

HRID 1275241 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)([C:17]#[N:18])[CH2:13][CH2:12]1)(C)(C)C.[OH:27]S(O)(=O)=O>>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)([C:17]([NH2:18])=[O:27])[CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 54428135HCID 54428135, compound

Product 1

HCID 22993440HCID 22993440, compoundYield 79%

Procedure

(+)-3-(3-(4-Aminocarbonyl-4-(4-chloro)phenylpiperidin-1-yl)-propyl)aminocarbonyl-4-(3,4-difluoro)phenyl-2-oxazolidinone: 3-(4-(4-chlorophenyl)-4-cyanopiperidin-1-yl)propylcarbamic acid tert-butyl ester (0.150 g, 5.39 mmol) in conc. H2SO4 (1 mL) was stirred at room temperature for 30 hours. The solution was concentrated, neutralized with 10% KOH solution and extracted into 25 mL of dichloromethane. The organic layer was dried over sodium sulfate, filtered and concentrated to give 0.185 g (79%) of 1-(3-aminopropyl)-4-(4-chlorophenyl)piperidine-4-carboxamide which was used as such for the subsequent step.

Workup

  1. concentrationThe solution was concentrated
  2. extractionextracted into 25 mL of dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-85e63cd520584bc3872d0b58490258ef
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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