1-Bromo-4-fluorobenzene → 1-BOC-4-(4-bromophenoxy)piperidine

HRID 912731Notes

Reaction equation

HRID 912731 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Br:15][C:16]1[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=1.[H-].[Na+]>CN(C)C=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 99931-Bromo-4-fluorobenzeneHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 467390061-BOC-4-(4-bromophenoxy)piperidineYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2.01 g (10 mmol) of 1,1-dimethylethyl 4-hydroxy-1-piperidinecarboxylate in 20 ml of dimethylformamide is admixed with 7 g (40 mmol) of 1-bromo-4-fluorobenzene and 2.5 g (50 mmol) of sodium hydride at 50% in mineral oil. The mixture is stirred at 100° C. for 3 hours and then evaporated to dryness. The residue is taken up in 50 ml of ice-water and extracted with dichloromethane. The organic extracts are evaporated to dryness, to give 3.5 g of an oily product, which is used as it is in the following step.

Workup

  1. customevaporated to dryness
  2. extractionextracted with dichloromethane
  3. customThe organic extracts are evaporated to dryness

Sources & evidence

ORD record
ord-0f140603e0394309894e324b9534237a
Source dataset
uspto-grants-2011_09
Patent number
US08026258B2

Reaction notes

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