4-(Aminomethyl)piperidine → HCID 13402008, compound

HRID 978497Notes

Reaction equation

HRID 978497 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)] were 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-(aminomethy)-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-54b24a90962e45a3965514afa02678f1
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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