Water → HCID 60064147, compound

HRID 412541Notes

Reaction equation

HRID 412541 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+].O.[C:28](Cl)(=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:28]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:37])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

Product 1

HCID 60064147HCID 60064147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-aminophenoxy)piperidine-1-carboxylic acid tert-butyl ester (6.63 g) and sodium hydrogencarbonate (2.1 g) in a mixture of tetrahydrofuran (100 ml)-water (100 ml) was dropwise added benzyl chlorocarbonate (3.24 ml), and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained residue was washed with diisopropyl ether, collected by filtration, and dried under reduced pressure to give the title compound (7.189 g).

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. washThe obtained residue was washed with diisopropyl ether
  7. filtrationcollected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-751bafd0709641e3b7a588d61c85bfe4
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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