Hydrochloric Acid → HCID 66720539, compound

HRID 220209Notes

Reaction equation

HRID 220209 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)(C)(C)C.[ClH:20].O1CCCC1>CO.C(O)(C)C>[Cl-:20].[CH:14]1([N:11]2[CH2:10][CH2:9][CH:8]([NH3+:7])[CH2:13][CH2:12]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid4×HCID 8028TetrahydrofuranHCID 53255879tert-Butyl (1-cyclopentylpiperidin-4-yl)carbamate

Product 1

HCID 66720539HCID 66720539, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 3776IsopropanolSolvent4×

Procedure

(1-Cyclopentyl-piperidin-4-yl)-carbamic acid tert-butyl ester (3) (6.70 g, 25 mmol, 1 equiv) was dissolved in methanol (30 mL), followed by the addition of 6 N HCl in isopropanol (10 mL). The solution was stirred at room temperature for 24 hours. Due to the incompleteness of the reaction, 6 N HCl in isopropanol (10 mL) and methanol (50 mL) were added to the solution. The solution was stirred at room temperature for another 24 hours. LC-MS indicated incompletion of the reaction. Tetrahydrofurane (20 mL), 6 N HCl in isopropanol (10 mL) and methanol (200 mL) were added to the solution. The solution was stirred at room temperature for 5 hours, followed by the addition of 6 N HCl in isopropanol (10 mL). The solution was stirred at room temperature for 72 hours. The solution was evaporated under reduced pressure to obtain 4 (4.20 g, 25 mmol, quantitative). LRMS (ES+): m/z 169.

Workup

  1. additionwere added to the solution
  2. stirringThe solution was stirred at room temperature for another 24 hours
  3. customincompletion of the reaction
  4. stirringThe solution was stirred at room temperature for 5 hours
  5. stirringThe solution was stirred at room temperature for 72 hours
  6. customThe solution was evaporated under reduced pressure
  7. customto obtain 4 (4.20 g, 25 mmol, quantitative)

Sources & evidence

ORD record
ord-30f56bc11eca4ae782e7e90ca5f09b79
Source dataset
uspto-grants-2012_06
Patent number
US08202887B2

Reaction notes

Loading…