Hydrochloric Acid → 2-(Piperidin-1-yl)aniline

HRID 2410304Notes

Reaction equation

HRID 2410304 reaction equation
Cl.[Sn](Cl)Cl.[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)([O-])=O.C(=O)(O)[O-].[Na+]>CO>[N:14]1([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH2:5])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 2254571-(2-Nitrophenyl)piperidineHCID 516892Sodium Bicarbonate

Product 1

HCID 4587952-(Piperidin-1-yl)anilineYield 88.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (1.50 ml, 18.0 mmol) and anhydrous tin dichloride (1.45 g, 7.64 mmol) were sequentially added at 0° C. to a methanol (10 ml) solution of 1-(2-nitrophenyl)piperidine (315 mg, 1.52 mmol) obtained as described in Referential Example 18-1. The resulting mixture was warmed to room temperature and stirred for 17 hours. A saturated aqueous solution of sodium bicarbonate was added to the mixture. The resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20 g, hexane/ethyl acetate=15/1). Thus, 2-(1-piperidinyl)aniline (238 mg, 88.8%) was yielded as a pale yellow oily material.

Workup

  1. customobtained
  2. extractionThe resulting mixture was extracted three times with ethyl acetate
  3. washThe obtained organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (20 g, hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-2de8c9bbe2564dcfb17a7f10deb5ba35
Source dataset
uspto-grants-2014_08
Patent number
US08816089B2

Reaction notes

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