Diethylamine → N,N-Diethyl-4-piperidinecarboxamide

HRID 731923Notes

Reaction equation

HRID 731923 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18].C(N(CC)CC)C.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH2:17]([N:19]([CH2:20][CH3:21])[C:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:16])[CH3:18]

Participants

7

Reactant 5

HCID 8021DiethylamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 410920N,N-Diethyl-4-piperidinecarboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-tert-butoxycarbonylpiperidine-4-carboxylic acid (5 g, 22.0 mmol) in DMF (100 mL) was added diethyl amine (4.6 mL, 44 mmol), triethylamine (9.1 mL, 66.0 mmol), HOAt (22.0 mL, 0.5 M in DMF, 22.0 mmol) and finally EDCI (8.4 g, 44 mmol). This was allowed to stir for 14 hours at room temperature. The solvent was then removed under reduced pressure. The mixture was taken up in DCM (100 mL). The organic layer was then washed with water (100 mL), 1N HCl (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. To the organic layer was added TFA (33 mL). The reaction was allowed to stir at room temperature for 2 hours. The solvent was then removed under reduced pressure. The mixture was taken up in DCM (100 mL). The organic layer was then washed with 1N NaOH (100 mL), water (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was sufficiently pure to use without further purification. The title compound was obtained in 86% yield (3.5 g, 19.0 mmol).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. washThe organic layer was then washed with water (100 mL), 1N HCl (100 mL), NaCl (sat.) (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. additionTo the organic layer was added TFA (33 mL)
  6. stirringto stir at room temperature for 2 hours
  7. customThe solvent was then removed under reduced pressure
  8. washThe organic layer was then washed with 1N NaOH (100 mL), water (100 mL), NaCl (sat.) (100 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customThe solvent was removed under reduced pressure
  12. customto use without further purification

Sources & evidence

ORD record
ord-9b28929f449c48b8802a331e567908a8
Source dataset
uspto-grants-2009_09
Patent number
US07585879B2

Reaction notes

Loading…