4-(Aminomethyl)piperidine → HCID 13402008, compound

HRID 1198575Notes

Reaction equation

HRID 1198575 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].[NH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(#N)C>[NH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:2]2[N:11]=[C:10]3[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]3[CH2:12][CH3:13])=[CH:4][C:3]=2[F:18])[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 235274-(Aminomethyl)piperidineHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 13402008HCID 13402008, compoundYield 634.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.52 g (0.19 mmole) of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8 -naphthyridine-3-carboxylic acid, 150 mL acetonitrile, and 0.66 g (5.76 mmole) 4-aminomethylpiperidine [J. Med. Chem., 9 441 (1966)] was stirred at room temperature for four days. The reaction was filtered and the precipitate dissolved in 500 mL of aqueous ammonium hydroxide at pH 10.5. The solution was filtered and the solvent was removed at reduced pressure. The precipitate was washed with 5 mL of water, then ether until dry to give 0.42 g of 7-[4-(aminomethyl)-1-piperidinyl]-1-ethyl-6-fluoro-1,4-dihydro-4 -oxo-1,8-naphthyridine-3-carboxylic acid, mp 203°-206° C.

Workup

  1. filtrationThe reaction was filtered
  2. dissolutionthe precipitate dissolved in 500 mL of aqueous ammonium hydroxide at pH 10.5
  3. filtrationThe solution was filtered
  4. customthe solvent was removed at reduced pressure
  5. washThe precipitate was washed with 5 mL of water
  6. dry with materialether until dry

Sources & evidence

ORD record
ord-3e56eaca3f51404ca1b6a2b87000785d
Source dataset
uspto-grants-1994_01
Patent number
US05281612

Reaction notes

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