Water → Ethyl 4-(4-(benzyloxycarbonylamino)piperidin-1-yl)benzoate

HRID 1615393Notes

Reaction equation

HRID 1615393 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH2:25]([O:32][C:33](Cl)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>C1COCC1>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][CH:14]([NH:17][C:33]([O:32][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:34])[CH2:15][CH2:16]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 22557718Ethyl 4-(4-aminopiperidin-1-yl)benzoate

Product 1

HCID 66691942Ethyl 4-(4-(benzyloxycarbonylamino)piperidin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 4-(4-aminopiperidin-1-yl)-benzoic acid ethyl ester (15.7 g, 63.2 mmol) obtained in Example 7(1) was dissolved in THF (200 ml), and a 2M sodium carbonate aqueous solution (63 ml) was added thereto. Subsequently, benzyloxycarbonyl chloride (11.7 ml, 82.2 mmol) was added thereto, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated sodium chloride, and then dried over anhydrous sodium sulfate. After the desiccant was filtered off, the solid obtained by evaporation under reduced pressure was collected by filtration and dried under reduced pressure, thereby obtaining 4-(4-benzyloxycarbonylaminopiperidin-1-yl)-benzoic acid ethyl ester (18.0 g, 74%) as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe solid obtained by evaporation under reduced pressure
  6. filtrationwas collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-feb08f97bd674ff7bcfd344a649b6494
Source dataset
uspto-grants-2014_07
Patent number
US08765750B2

Reaction notes

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