Water → N-[(1-tert-butoxycarbonyl-4-piperidyl)methyl]pyridine-2-carboxamide

HRID 1584879Notes

Reaction equation

HRID 1584879 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[NH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.O>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([CH2:11][NH:10][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])[CH2:13][CH2:14]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 962WaterHCID 1018Picolinic acidHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 21221065N-[(1-tert-butoxycarbonyl-4-piperidyl)methyl]pyridine-2-carboxamideYield 36.1%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of pyridine-2-carboxylic acid (2.7 g) and 4-(aminomethyl)-1-tert-butoxycarbonylpiperidine (5.0 g) in dry xylene (50 ml) was heated under reflux under a Dean and Stark water separator for six hours. The cooled solution was diluted with ethyl acetate (150 ml), washed with aqueous oxalic acid solution (2M; 2×100 ml) then aqueous sodium hydrogen carbonate soultion (5M; 2×100 ml) and dried over magnesium sulphate. The solvent was removed in vacuo to give N-[(1-tert-butoxycarbonyl-4-piperidyl)methyl]pyridine-2-carboxamide (2.53 g) as an oil.

Workup

  1. temperaturewas heated
  2. washwashed with aqueous oxalic acid solution (2M; 2×100 ml)
  3. dry with materialaqueous sodium hydrogen carbonate soultion (5M; 2×100 ml) and dried over magnesium sulphate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d7fbf6e4e6a4460bbc655736ba322da8
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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