Potassium Carbonate → tert-Butyl (1-cyclopentylpiperidin-4-yl)carbamate

HRID 220208Notes

Reaction equation

HRID 220208 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].I[CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 73784Iodocyclopentane2×HCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 53255879tert-Butyl (1-cyclopentylpiperidin-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This compound was synthesized from the commercially available piperidin-4-yl-carbamic acid tert-butyl ester (2) (5 g, 25 mmol, 1 equiv) which was dissolved in acetonitrile (150 mL), followed by the addition of iodo-cyclopentane (9.79 g, 50 mmol, 2 equiv) and K2CO3 (3.45 g, 25 mmol, 1 equiv). The solution was stirred at room temperature for 48 hours. Due to the incompleteness of the reaction, iodocyclo-pentane (1.70 g, 8.69 mmol, 0.35 equiv) and K2CO3 (1 g, 7.25 mmol, 0.29 equiv) were added to the solution. The solution was stirred at room temperature for several hours. The solution was filtered over a bed of dicalite and the filtrate was evaporated under reduced pressure to obtain 3 (6.70 g, 25 mmol, quantitative). LRMS (ES+): m/z 269.

Workup

  1. additionwere added to the solution
  2. stirringThe solution was stirred at room temperature for several hours
  3. filtrationThe solution was filtered over a bed of dicalite
  4. customthe filtrate was evaporated under reduced pressure
  5. customto obtain 3 (6.70 g, 25 mmol, quantitative)

Sources & evidence

ORD record
ord-9c998cb6ea894466b8b45319bb1fbd67
Source dataset
uspto-grants-2012_06
Patent number
US08202887B2

Reaction notes

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