tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylate → N-(3-fluorophenyl)piperidin-4-amine

HRID 883761Notes

Reaction equation

HRID 883761 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1>Cl.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 23137591tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylate

Product 1

HCID 4778195N-(3-fluorophenyl)piperidin-4-amineYield 87.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl 4-[(3-fluorophenyl)amino]-1-piperidinecarboxylate (D3) (2.30 g) in 2M HCl (5 ml) and 1,4-dioxane (40 ml) was heated at 70° C. with stirring overnight. On cooling, the solvent was removed in vacuo and the residue diluted with 2M NaOH solution and extracted with 9:1 EtOAc/tBuOH (×2). The organics were dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow solid (1.33 g). δH (CDCl3, 250 MHz) 7.07 (1H, q), 6.33 (3H, m), 3.83 (1H, br s), 3.33 (1H, br s), 3.12 (2H, m), 2.71 (2H, m), 2.04 (2H, m), 1.30 (2H, m).

Workup

  1. temperatureOn cooling
  2. customthe solvent was removed in vacuo
  3. additionthe residue diluted with 2M NaOH solution
  4. extractionextracted with 9:1 EtOAc/tBuOH (×2)
  5. dry with materialThe organics were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d98bbe2ad5048108e8e4c5868449187
Source dataset
uspto-grants-2012_08
Patent number
US08236953B2

Reaction notes

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