Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride → HCID 178517476, compound

HRID 1272376Notes

Reaction equation

HRID 1272376 reaction equation
[Na].[O-]CC.[Na+].Cl.[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]([O:22]CC)=O)[C:16](=O)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[F:27][C:28]([F:39])([F:38])[C:29]1[N:34]=[CH:33][C:32]([C:35]([NH2:37])=[NH:36])=[CH:31][CH:30]=1>C(O)C>[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]2[C:20]([OH:22])=[N:37][C:35]([C:32]3[CH:33]=[N:34][C:29]([C:28]([F:39])([F:27])[F:38])=[CH:30][CH:31]=3)=[N:36][C:16]=2[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 2723880Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochlorideHCID 2723922Sodium ethoxideHCID 27607776-(Trifluoromethyl)pyridine-3-carboximidamide--hydrogen chloride (1/1)HCID 5360545Sodium

Product 1

HCID 178517476HCID 178517476, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 258 mg (11.2 mmol) of sodium in 10 mL of absolute ethanol was stirred at ambient temperature for 1 h. To the resultant sodium ethoxide solution was added 893 mg (3.0 mmol) of ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride in portions followed by 840 mg (3.72 mmol) of 6-(trifluoromethyl)pyridine-3-amidine hydrochloride. The reaction mixture was heated at reflux for 18 h, then concentrated in vacuo. To the residue was added ˜30 mL of 1N aqueous sodium hydroxide solution and 15 mL of water to give an insoluble solid and a yellow solution. The solid was filtered off and washed with water to provide 496 mg of the title compound. The aqueous filtrate was acidified to ˜pH 5 with concentrated hydrochloric acid and the solid precipitate was collected to give an additional 334 mg of the title compound as a bright yellow powder (72% total yield). LC-MS 387.2 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. additionTo the residue was added ˜30 mL of 1N aqueous sodium hydroxide solution and 15 mL of water
  5. customto give an insoluble solid
  6. filtrationThe solid was filtered off
  7. washwashed with water

Sources & evidence

ORD record
ord-1bab5d7d37984cec98fef6f491c864da
Source dataset
uspto-grants-2007_04
Patent number
US07208498B2

Reaction notes

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