Hydrochloric Acid → N-(4-chlorophenyl)piperidin-4-amine

HRID 1430083Notes

Reaction equation

HRID 1430083 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH: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.[OH-].[Na+]>C(OCC)(=O)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1491503Tert-butyl 4-(4-chlorophenylamino)piperidine-1-carboxylate

Product 1

HCID 7183033N-(4-chlorophenyl)piperidin-4-amineYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The tert-butyl-4-(4-chlorophenylamino)piperidine-1-carboxylate (973.2 mg, 3.1 mmol) obtained in step 1 was dissolved in ethyl acetate and mixed at 0 C for 3 hr with 6N HCl (5 mL), with stirring, after which distilled water was added to terminate the reaction. The resulting reaction mixture was washed with ethyl acetate. The pH of the aqueous layer thus formed was adjusted to 10 to 12 with 2N sodium hydroxide, followed by washing with ethyl acetate and saline to separate an organic solvent layer. This organic solvent layer was dried over anhydrous magnesium sulfate and evaporated at reduced pressure to afford N-(4-chlorophenyl)piperidine-4-amine (yield 87%).

Workup

  1. distillationafter which distilled water
  2. additionwas added
  3. customto terminate
  4. customthe reaction
  5. customThe resulting reaction mixture
  6. washwas washed with ethyl acetate
  7. customThe pH of the aqueous layer thus formed
  8. washby washing with ethyl acetate and saline
  9. customto separate an organic solvent layer
  10. dry with materialThis organic solvent layer was dried over anhydrous magnesium sulfate
  11. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-1c302b76bed047498f421dd13befd1f5
Source dataset
uspto-grants-2015_01
Patent number
US08940768B2

Reaction notes

Loading…