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

HRID 43337Notes

Reaction equation

HRID 43337 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-piperidinamine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 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 (0.719). 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), 1.62 (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-5e2e031076cd46738caed69ef5e27215
Source dataset
uspto-grants-2013_09
Patent number
US08536182B2

Reaction notes

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