p-Fluoronitrobenzene → Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate

HRID 1403713Notes

Reaction equation

HRID 1403713 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[OH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[K+]>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([O:11][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:13][CH2:14]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 2794776Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylateYield 109.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

1-Fluoro-4-nitrobenzene (10.0 g, 70.9 mmol) was melted into 4-hydroxy-1-Boc-piperidine (12.97 g, 64.4 mmol). The mixture obtained was treated with a 25 wt % potassium hydroxide solution (60 mL) and tetrabutylammonium bromide (1.60 g, 4.96 mmol) and heated at 40° C. for 70 hours. The precipitate was collected by filtration, washed with water and air-dried to leave the title compound (22.7 g, quantitative yield) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.20 (m, 2H), 6.95 (m, 2H), 4.60 (m, 1H), 3.70 (m, 2H), 3.38 (m, 2H), 1.97 (m, 2H), 1.78 (m, 2H), 1.48 (s, 9H).

Workup

  1. customThe mixture obtained
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-54d8abe1c5644e19ad31073cdebeee60
Source dataset
uspto-grants-2014_12
Patent number
US08912219B2

Reaction notes

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