tert-Butyl 4-(3-bromophenoxy)piperidine-1-carboxylate → HCID 22492895, compound

HRID 1816330Notes

Reaction equation

HRID 1816330 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)C=1.[CH3:22][OH:23].C[O-].[Na+]>CO>[CH3:22][O:23][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 22492957tert-Butyl 4-(3-bromophenoxy)piperidine-1-carboxylateHCID 23694274Sodium methanolate methanol

Product 1

HCID 22492895HCID 22492895, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(5-bromophenyloxy)-1-piperidinecarboxylate (12.98 g) in methanol (70 ml) was added 28% sodium methoxide methanol solution (37.8 ml) and the mixture was stirred under refluxing for 4 hours. After cooling, the reaction mixture was evaporated in vacuo. The resulting residue was chromatographed on silica gel (400 ml) eluting with a mixture of n-hexane and ethyl acetate (5:1 v/v). The fractions containing the object compound were collected and evaporated under reduced pressure to give tert-butyl 4-(5-methoxypentyloxy)-1-piperidinecarboxylate (16.31 g). This compound was immediately used as the starting compound for the next step.

Workup

  1. temperatureunder refluxing for 4 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated in vacuo
  4. customThe resulting residue was chromatographed on silica gel (400 ml)
  5. washeluting with a mixture of n-hexane and ethyl acetate (5:1 v/v)
  6. additionThe fractions containing the object compound
  7. customwere collected
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1353573013524c07b1d20d0d8bd2c8ae
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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