Diethylamine → 3-(Boc-amino)piperidine

HRID 501411Notes

Reaction equation

HRID 501411 reaction equation
C(NCC)C.[C:6]([O:10][C:11]([NH:13][CH:14]1[CH2:19][CH2:18][CH2:17][N:16](C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[CH2:15]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>C(O)C>[NH:16]1[CH2:17][CH2:18][CH2:19][CH:14]([NH:13][C:11](=[O:12])[O:10][C:6]([CH3:8])([CH3:7])[CH3:9])[CH2:15]1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 23070937HCID 23070937, compound

Product 1

HCID 42330413-(Boc-amino)piperidineYield 88.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25 ml of diethylamine was added to 250 ml of an ethanol solution of 1.88 g of 9H-fluoren-9-ylmethyl 3-t-butoxycarbonylaminopiperidine-1-carboxylate, and the mixture was stirred at room temperature for 18 hours. After the solution had been concentrated under reduced pressure, the residue was dissolved in a mixture consisting of 150 ml of toluene and 100 ml of 10% aqueous citric acid solution. The aqueous layer was made alkaline with a 5N aqueous sodium hydroxide solution, and then extracted twice with 100 ml of dichloromethane. The organic layers were combined together, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 0.79 g of the title compound.

Workup

  1. concentrationAfter the solution had been concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture
  3. extractionextracted twice with 100 ml of dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d8aeda4238644949a7c71f8691229e49
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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