Hydrochloric Acid → HCID 10516402, compound

HRID 1042323Notes

Reaction equation

HRID 1042323 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][C@@H](N)C1C=CC=CC=1.[CH3:25][C:26]([CH:28]=C)=[O:27].C1(C=CC(O)=CC=1)O.Cl>C1(C)C=CC=CC=1.C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C@:10]([CH3:16])([CH2:15][CH2:25][C:26](=[O:27])[CH3:28])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 6570Methyl vinyl ketoneHCID 5609651-Benzyl-3-methyl-4-piperidoneHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 10516402HCID 10516402, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl-3-methyl-piperidin-4-one (15.0 g, 73.89 mmol) was dissolved in toluene (150 mL) and (R)-(+)-α-methylbenzylamine (11.4 mL, 88.67 mmol) was added. The contents were heated to reflux for 20 h (Dean-Stark trap) and then cooled to room temperature. The resultant colorless oil was dissolved in THF and methylvinylketone (7.40 mL, 88.67 mmol) and hydroquinone (150 mg, catalytic) were added and the contents were stirred in the dark. After 2 days 1N HCl (90 mL) was added and the contents stirred at ambient temperature for 30 min, the organics were extracted with diethyl ether (100 mL), washed with water, dried with MgSO4, concentrated and purified by flash chromatography (CH2Cl2 100% to 20% EtOAc in CH2Cl2) to afford 6.51 g of ((R)-1-benzyl-3-methyl-3-(3-oxo-butyl)-piperidin-4-one as a colorless oil. LC-MS (Method A): RT=0.32 min, (M+H)+ 274.

Workup

  1. temperatureThe contents were heated
  2. temperatureto reflux for 20 h (Dean-Stark trap)
  3. stirringthe contents stirred at ambient temperature for 30 min
  4. extractionthe organics were extracted with diethyl ether (100 mL)
  5. washwashed with water
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography (CH2Cl2 100% to 20% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-b91d57c290b1425b93b009b81c3945e2
Source dataset
uspto-grants-2013_10
Patent number
US08557839B2

Reaction notes

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