Sodium Hydroxide → N-(4-Fluorophenyl)-4-piperidinamine

HRID 906338Notes

Reaction equation

HRID 906338 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[OH-].[Na+]>Cl.O1CCOCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 16413902tert-Butyl 4-(4-fluoroanilino)piperidine-1-carboxylate

Product 1

HCID 4778193N-(4-Fluorophenyl)-4-piperidinamineYield 67.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl 4-[(4-fluorophenyl)amino]-1-piperidinecarboxylate (D1) (1.6 g) in 2M HCl (5 ml) and 1,4-dioxane (20 ml) was heated at 60° C. for 24 h. On cooling, the solution was diluted with water, basified with 2M NaOH solution and extracted with EtOAc (×3). The combined organics were dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow oil (0.71 g). δH (CDCl3, 250 MHz) 6.88 (2H, t), 6.54 (2H, dd), 3.30 (1H, m), 3.20 (2H, m), 2.70 (2H, m), 2.05 (2H, m), 1.69 (2H, br), 1.29 (2H, m).

Workup

  1. temperatureOn cooling
  2. extractionextracted with EtOAc (×3)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15ec08bdeddf4213855c57818faccfb1
Source dataset
uspto-grants-2011_09
Patent number
US08012981B2

Reaction notes

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