4-Chloroaniline → Tert-butyl 4-(4-chlorophenylamino)piperidine-1-carboxylate

HRID 1430082Notes

Reaction equation

HRID 1430082 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.[Na]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([Cl:15])=[CH:17][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 78124-ChloroanilineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5360545Sodium

Product 1

HCID 1491503Tert-butyl 4-(4-chlorophenylamino)piperidine-1-carboxylateYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl-4-oxopiperidine-1-carboxylate (1.0 g, 0.005 mmol) in tetrahydrofuran (16 mL) in a microwave reaction vessel were added 4-chloroaniline (640 mg, 0.005 mmol) and sodium triacetoxyboryhidride (3.2 g, 0.015 mmol), followed by irradiating the solution with microwaves at 80° C. for 10 min. The reaction was terminated by the addition of distilled water. The resulting reaction mixture was diluted in ethyl acetate (100 mL) and washed with distilled water (200 mL) to separate an organic solvent layer. The organic solvent layer was dried over anhydrous magnesium sulfate and evaporated at reduced pressure. Isolation and purification of the residue through silica gel chromatography produced tert-butyl-4-(4-chlorophenylamino)piperidine-1-carboxylate (yield: 65%).

Workup

  1. customby irradiating the solution with microwaves at 80° C. for 10 min
  2. customThe reaction was terminated by the addition of distilled water
  3. customThe resulting reaction mixture
  4. washwashed with distilled water (200 mL)
  5. customto separate an organic solvent layer
  6. dry with materialThe organic solvent layer was dried over anhydrous magnesium sulfate
  7. customevaporated at reduced pressure
  8. customIsolation and purification of the residue through silica gel chromatography

Sources & evidence

ORD record
ord-b9fddc04b42d474a88bf7a375c355bb5
Source dataset
uspto-grants-2015_01
Patent number
US08940768B2

Reaction notes

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