1,6-Dibromohexane → HCID 18434316, compound

HRID 2306501Notes

Reaction equation

HRID 2306501 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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 18434316HCID 18434316, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 7 g of tert-butyl (4-hydroxy)-piperidine-1-carboxylate and 210 ml of 1,6-dibromohexane is treated firstly with 3.5 g of tetrabutylammonium hydrogen sulphate and then with 210 ml of 50% aqueous sodium hydroxide solution. After stirring at room temperature for 5 days the reaction mixture is diluted with methylene chloride, the organic phase is separated and the aqueous phase is extracted with methylene chloride. The combined organic phases are washed with saturated sodium chloride solution, dried and concentrated. The brown oil is chromatographed on silica gel with ethyl acetate-hexane. 10.9 g of tert-butyl 4-(6-bromo-hexyloxy)-piperidine-1-carboxylate are obtained.

Workup

  1. customthe organic phase is separated
  2. extractionthe aqueous phase is extracted with methylene chloride
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customThe brown oil is chromatographed on silica gel with ethyl acetate-hexane

Sources & evidence

ORD record
ord-5541e5432f7f40b6976395bd9d812fc5
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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