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

HRID 2424414Notes

Reaction equation

HRID 2424414 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 74.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of D1 (1.44 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) 1.29 (2H, m), 2.05 (2H, m), 2.70 (2H, m), 3.20 (1H, m), 3.30 (2H, m), 6.54 (2H, dd), 6.88 (2H, t).

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-9af9056896cb4d6db5ca0c09c198a935
Source dataset
uspto-grants-2011_06
Patent number
US07964602B2

Reaction notes

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