Hydrochloric Acid → 4-(4-Chlorobenzyl)piperidine

HRID 1016436

Reaction equation

HRID 1016436 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 22893851Tert-butyl 4-(4-chlorobenzyl)piperidine-1-carboxylate

Product 1

HCID 37327804-(4-Chlorobenzyl)piperidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2 g of 4-(4-chloro-benzyl)-piperidine-1-carboxylic acid tert-butyl ester, dioxane (1.5 mL), and 3N hydrochloric acid (1.0 mL, 4equiv.) was heated at reflux for 3.5 hours. The cooled mixture was made basic with saturated sodium carbonate solution and extracted with chloroform (3×10 mL). The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The crude product (1.2 g) was an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. extractionextracted with chloroform (3×10 mL)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a322db343dac44d1a4ef02ca7f9d00c2
Source dataset
uspto-grants-2002_11
Patent number
US06476041B1

Linked notes

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