1,6-Dibromohexane → HCID 22494777, compound

HRID 1816709Notes

Reaction equation

HRID 1816709 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15](=O)[CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.C[O-].[Na+].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27]CCBr>C1COCC1.CO>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:16][CH2:15][S:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 22494773tert-Butyl 4-(acetylthio)piperidine-1-carboxylateHCID 23694274Sodium methanolate methanol

Product 1

HCID 22494777HCID 22494777, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-t-butyloxycarbonyl-4-acetylthiopiperidine (5.5 g) in a mixture of THF (50 ml) and methanol (50 ml) was added 28% sodium methoxide methanol solution (4.76 ml) with stirring under ice-cooling and stirred at the same temperature for 30 minutes. To the solution was added 1,6-dibromohexane (17.1 g) under ice-cooling, and the mixture was successively stirred at ambient temperature for 30 minutes and then stirred at 45° C. for 2 hours. The reaction mixture was concentrated in vacuo. The resulting residue was chromatographed on silica gel (500 ml) eluting with a mixture of n-hexane and ethyl acetate (6:1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give 4-(6-bromohexylthio)-N-t-butyloxycarbonylpiperidine (4.95 g).

Workup

  1. temperaturecooling
  2. stirringstirred at the same temperature for 30 minutes
  3. temperaturecooling
  4. stirringthe mixture was successively stirred at ambient temperature for 30 minutes
  5. stirringstirred at 45° C. for 2 hours
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customThe resulting residue was chromatographed on silica gel (500 ml)
  8. washeluting with a mixture of n-hexane and ethyl acetate (6:1 v/v)
  9. additionThe fractions containing the desired compound
  10. customwere collected
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3c31a3570e304b03ac9034aa2b60d7a3
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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