Potassium Carbonate → HCID 67442456, compound

HRID 1667321Notes

Reaction equation

HRID 1667321 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([NH:7]C(=O)OC(C)(C)C)[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:21][CH2:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28](/[CH:31]=[CH:32]/[C:33]2[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:40])[CH2:27][CH2:26]1)=[O:24]>C(#N)C>[ClH:21].[ClH:21].[CH3:40][C:34]1[CH:35]=[CH:36][CH:37]=[C:38]([CH3:39])[C:33]=1/[CH:32]=[CH:31]/[CH:28]1[CH2:29][CH2:30][N:25]([C:23](=[O:24])[CH2:22][N:1]2[CH2:6][CH2:5][CH2:4][C@H:3]([NH2:7])[CH2:2]2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 10402058HCID 10402058, compound

Product 1

HCID 67442456HCID 67442456, compoundYield 161.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

329 mg of tert-butyl (3S)-piperidin-3-ylcarbamate and 189 mg of potassium carbonate were added to a solution of 400 mg of 1-(chloroacetyl)-4-[(E)-2-(2,6-dimethylphenyl)vinyl]piperidine in 10 ml of acetonitrile, followed by heating under reflux for 2 hours. After the reaction mixture was concentrated under reduced pressure, chloroform and saturated aqueous sodium hydrogencarbonate solution were added to the residue, then the organic layer was fractionated. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol-ammonia water). The obtained oil was dissolved in 10 ml of ethanol, and 10 ml of 4N hydrochloric acid-ethyl acetate was added to the solution, followed by stirring at ambient temperature for 3 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was crystallized from 2-propanol-diisopropyl ether. The crystals were recrystallized from water-ethanol to give 473 mg of (3S)-1-(2-{4-[(E)-2-(2,6-dimethylphenyl)vinyl]piperidin-1-yl}-2-oxoethyl)piperidine-3-amine dihydrochloride.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure, chloroform and saturated aqueous sodium hydrogencarbonate solution
  4. additionwere added to the residue
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol-ammonia water)
  7. dissolutionThe obtained oil was dissolved in 10 ml of ethanol
  8. addition10 ml of 4N hydrochloric acid-ethyl acetate was added to the solution
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. customthe resulting residue was crystallized from 2-propanol-diisopropyl ether
  11. customThe crystals were recrystallized from water-ethanol

Sources & evidence

ORD record
ord-8f3f1c567f614140b6d668ee52d397f8
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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