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Hydrochloric Acid → 1-[(1S)-1-(2-Naphthalenyl)ethyl]-4-piperidinone

HRID 897225
Notes
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Reaction equation

HRID 897225 reaction equation
COC(=O)[CH2:4][CH2:5][N:6]([CH2:19][CH2:20][C:21]([O:23]C)=O)[C@H:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[CH3:8].[H-].[Na+].Cl.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CC(O)=O>[CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[C@@H:7]([N:6]1[CH2:19][CH2:20][C:21](=[O:23])[CH2:4][CH2:5]1)[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 69697317HCID 69697317, compound

Product 1

HCID 697035741-[(1S)-1-(2-Naphthalenyl)ethyl]-4-piperidinoneYield 47.4%

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Solvent
HCID 1140TolueneSolvent

Procedure

To a solution of (S)-methyl-3-[(2-methoxycarbonylethyl)-(1-naphthalen-2-yl-ethyl)-amino]-propanoate (3.6 g, 10 mmol) in toluene (20 mL), NaH (0.5 g, 13 mmol) was added and the mixture was refluxed in an oil bath kept at 150° C. for 6 hours. After cool, the reaction mixture was acidified with AcOH and extracted with benzene. The organic layer was dried over MgSO4, and concentrated to afford a crude oil. The oil was boiled with 10% HCl (20 mL) for 18 hours. The aqueous solution was basified with K2CO3 and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated. The crude oil was purified by chromatography on silica gel with ethyl acetate/hexanes (1:4) to give the title compound (1.2 g, 47%). 1H NMR (300 MHz, CDCl3) δ 1.51 (3H, d, J=6.59 Hz), 2.44 (4H, t, J=6.03 Hz), 2.71-2.90 (4H, m), 3.79 (1H, q, J=6.78 Hz), 7.42-7.60 (3H, m), 7.72-7.86 (4H, m).

Workup

  1. temperaturethe mixture was refluxed in an oil bath
  2. temperatureAfter cool
  3. extractionextracted with benzene
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customto afford a crude oil
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried over MgSO4
  9. customevaporated
  10. customThe crude oil was purified by chromatography on silica gel with ethyl acetate/hexanes (1:4)

Sources & evidence

ORD record
ord-beff979d26fb42cdb32b555b234122e8
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06921821B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes