Sulfuric Acid → HCID 22993440, compound

HRID 1167725Notes

Reaction equation

HRID 1167725 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-(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-ab00e7eaede547ae9e6e20a6ca28ed40
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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