Hydrochloric Acid → HCID 66731842, compound

HRID 1963298Notes

Reaction equation

HRID 1963298 reaction equation
Cl.[Cl:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([OH:16])=[O:15])[CH2:11][CH2:10][NH:9]2)=[CH:5][CH:4]=1.Cl.[C:20]([O-])(O)=O.[Na+]>>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([O:16][CH3:20])=[O:15])[CH2:11][CH2:10][NH:9]2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66732341HCID 66732341, compound

Product 1

HCID 66731842HCID 66731842, compoundYield 87%

Procedure

To crude 2-(4-chlorobenzyl)piperidine-4-carboxylic acid hydrochloride (5.34 g, 20.9 mmol) was added HCl (1.25 M in MeOH, 60 mL). The resulting suspension was refluxed for 2 h and then concentrated to give a slightly yellow solid. The residue was taken up in satd NaHCO3 (100 mL). The aqueous phase was extracted with DCM (×3), the combined organic layers dried with a phase separator and evaporated to yield methyl 2-(4-chlorobenzyl)piperidine-4-carboxylate (3.85 g, 87%) as a brown oil. MS m/z 268, 270 (M+H)+

Workup

  1. temperatureThe resulting suspension was refluxed for 2 h
  2. concentrationconcentrated
  3. customto give a slightly yellow solid
  4. extractionThe aqueous phase was extracted with DCM (×3)
  5. customthe combined organic layers dried with a phase separator
  6. customevaporated

Sources & evidence

ORD record
ord-6bbfff0a99904e8db4b51dd25a3b7cbf
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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