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4-Piperidinecarboxamide → benzyl 4-(aminocarbonyl)tetrahydro-1(2H)-pyridinecarboxylate

HRID 1497645
Notes
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Reaction equation

HRID 1497645 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:2]1.[CH2:10]([O:17][C:18](Cl)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>O.CC(C)=O>[CH2:10]([O:17][C:18]([N:1]1[CH2:6][CH2:5][CH:4]([C:7](=[O:8])[NH2:9])[CH2:3][CH2:2]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 2776131benzyl 4-(aminocarbonyl)tetrahydro-1(2H)-pyridinecarboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent
HCID 962
Water
Solvent

Procedure

To a solution of piperidine-4-carboxamide (5 g, 39 mmol) and benzylchloroformate (5.54 mL, 39 mmol) in a mixture of water (30 mL) and acetone (40 mL), NaOH 1N (39 mL, 39 mmol) was added dropwise, while maintaining the pH between 6 and 8. The mixture was stirred at r.t. for 3 h; then acetone was evaporated and the resulting precipitate filtered and dried at 70° C. under reduced pressure, giving 7.75 g of benzyl-4-carbamoylpiperidine-1-carboxylate (76%).

Workup

  1. additionwas added dropwise
  2. temperaturewhile maintaining the pH between 6 and 8
  3. customthen acetone was evaporated
  4. filtrationthe resulting precipitate filtered
  5. customdried at 70° C. under reduced pressure

Sources & evidence

ORD record
ord-7d8dfbdbecc44e4f9aa4d905818ba5ff
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09199979B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes