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

HRID 1791957Notes

Reaction equation

HRID 1791957 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.C(Cl)(=O)O[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:29](=O)([O-])[OH:30].[Na+]>ClCCl>[CH2:20]([O:19][C:29]([N:1]1[CH2:9][CH2:8][CH:4]([C:5](=[O:6])[NH2:7])[CH2:3][CH2:2]1)=[O:30])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 37724-PiperidinecarboxamideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 21874344HCID 21874344, compound

Product 1

HCID 2776131benzyl 4-(aminocarbonyl)tetrahydro-1(2H)-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isonipecotamide (19.4 g) and triethylamine (42 mL) were dissolved in dichloromethane (500 mL), and benzyloxy chlorocarbonate (24 mL) was added thereto under ice-cooling. The mixture was stirred at room temperature for 18 hr. The reaction mixture was added to saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with chloroform. The extract was dried and concentrated under reduced pressure to give 1-benzyloxycarbonyl-4-carbamoylpiperidine (33.3 g) as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. extractionthe mixture was extracted with chloroform
  3. customThe extract was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d863b73c392e4aa7ab2a5db34021dbe8
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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