1,4-Dibromobutane → HCID 53810368, compound

HRID 1816678Notes

Reaction equation

HRID 1816678 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:17][CH2:18][CH2:19][CH2:20][CH2:21]Br>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:21][CH2:20][CH2:19][CH2:18][Br:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 53810368HCID 53810368, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-hydroxypiperidine (6 g) in N,N-dimethylformamide (30 ml) was portion wise added sodium hydride (60%, 1.6 g) at 5° C. with stirring. The mixture was stirred at room temperature for 0.5 hour and at 60° C. for an hour. To the reaction mixture was added dropwise 1,4-dibromobutane (19 g) at 5° C. with stirring. The mixture was stirred at room temperature for 4 hours and at 50° C. for 2 hours. The reaction mixture was poured into ice-water and extracted with a mixture of ethyl acetate and tetrahydrofuran (1:1). The organic layer was washed with saturated sodium chloride aqueous solution and dried over magnesium sulfate. The magnesium sulfate was filtered under reduced pressure, and the filtrate was concentrated under reduced pressure to give oil. The oil was subjected to column chromatography on silica gel (silica gel 60 F254, Merck) and eluted with a mixture of ethyl acetate and n-hexane (1:10-1:3). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 1-(tert-butoxycarbonyl)-4-[(4-bromo)butoxy]piperidine (1.5 g).

Workup

  1. customat 5° C.
  2. stirringThe mixture was stirred at room temperature for 0.5 hour and at 60° C. for an hour
  3. stirringwith stirring
  4. stirringThe mixture was stirred at room temperature for 4 hours and at 50° C. for 2 hours
  5. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran (1:1)
  6. washThe organic layer was washed with saturated sodium chloride aqueous solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe magnesium sulfate was filtered under reduced pressure
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customto give oil
  11. washeluted with a mixture of ethyl acetate and n-hexane (1:10-1:3)
  12. additionThe fractions containing the objective compound
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a98e9e617bd4fa2831d2dc3147ce113
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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