Acetic Acid → tert-Butyl 4-(2-chloroanilino)piperidine-1-carboxylate

HRID 1868086Notes

Reaction equation

HRID 1868086 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][CH:20]=[CH:19][C:17]=1[NH2:18].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CC.C(Cl)CCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[Cl:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 72402-ChloroanilineHCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22557784tert-Butyl 4-(2-chloroanilino)piperidine-1-carboxylateYield 8.2%

Reagents, catalysts & solvents 1

HCID 20449178Ethylene chloride ethaneSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-4-piperidone (8.01 g, 39.4 mmol), 2-chloroaniline (5.74 g, 44.1 mmol) and acetic acid (2.80 g, 46.6 mmol) in 200 ml ethylene chloride ethane was added sodium triacetoxyborohydride (8.37 g, 78.8 mmol). The mixture was stirred at room temp for 2.5 days. Added 2N NaOH solution to adjust pH to 10. The organic phase was separated and washed with water, then dried over Na2SO4. Solvent was removed under vacuum and crude product was purified with flash column chromatography to yield tert-butyl-4-(2-chlorophenylamino)piperidine-1-carboxylate in 8.2% yield (1.6 g) as white solid.

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. customSolvent was removed under vacuum and crude product
  5. customwas purified with flash column chromatography

Sources & evidence

ORD record
ord-2e9f528fcc64443db6aed3b7237f2a67
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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