Sodium Carbonate → 1-BOC-4-(4-bromophenoxy)piperidine

HRID 341168

Reaction equation

HRID 341168 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[O:21](C(OC(C)(C)C)=O)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=O>O1CCOCC1.O>[C:25]([O:24][C:22]([N:10]1[CH2:9][CH2:8][CH:7]([O:6][C:5]2[CH:13]=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:12][CH2:11]1)=[O:21])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 126455664-(4-Bromophenoxy)piperidine

Product 1

HCID 467390061-BOC-4-(4-bromophenoxy)piperidineYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(4-Bromo-phenoxy)-piperidine (1 g, 3.9 mmol) in dioxane (20 ml), water (20 ml) added Na2CO3 (1.6 g, 18.9 mmol) and (BOC)2O (1.3 g, 5.9 mmol). Reaction stirred at ambient for 48 hours, solvent was removed under reduced pressure and residue partitioned between EtOAc and water the layers were separated. The organic layer was washed with brine, dried (MgSO4), and concentrated under reduced pressure to give (1.2 g) of product.

Workup

  1. customReaction
  2. customsolvent was removed under reduced pressure and residue
  3. custompartitioned between EtOAc and water the layers
  4. customwere separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c093a24d27e94e44a89572729fb84f14
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Linked notes

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