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Hydrochloric Acid → N-(2-Cyano-4-trifluoromethylphenyl)-4-piperidone

HRID 842780
Notes
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Reaction equation

HRID 842780 reaction equation
C1O[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=3[C:21]#[N:22])[CH2:7][CH2:6]2)[O:4]C1C.Cl.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>CCOCC>[C:21]([C:12]1[CH:13]=[C:14]([C:17]([F:19])([F:20])[F:18])[CH:15]=[CH:16][C:11]=1[N:8]1[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]1)#[N:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 86757962N-(2-Cyano-4-trifluoromethylphenyl)-4-piperidone propylene ketal

Product 1

HCID 22615393N-(2-Cyano-4-trifluoromethylphenyl)-4-piperidone

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

Procedure

A solution of 24 (1.70 g, 5.20 mmol) in ether (20 mL) was treated with 6N aqueous HCl (50 mL). The mixture was stirred at room temperature (20 min). The reaction mixture was neutralized with sodium carbonate solution and solid sodium hydroxide. The aqueous layer was extracted with two additional portions of ether and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 6 mm, 10% EtOH-90% CHCl3) afforded the title compound (25).

Workup

  1. extractionThe aqueous layer was extracted with two additional portions of ether
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-36f5e362280c44869be0b111c57c12b5
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06376503B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes