3-Pyrrolidinemethanamine → HCID 461884, compound

HRID 1198572Notes

Reaction equation

HRID 1198572 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].[NH:19]1[CH2:23][CH2:22][CH:21]([CH2:24][NH2:25])[CH2:20]1>C(#N)C>[NH2:25][CH2:24][CH:21]1[CH2:22][CH2:23][N:19]([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])[CH2:20]1

Participants

4

Reactant 2

HCID 50687753-PyrrolidinemethanamineHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 461884HCID 461884, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2 00 g (7.39 mmole) of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8 -napthyridine-3-carboxylic acid, 250 mL acetonitrile and 2.22 g (22.17 mmole) 3-pyrrolidinemethanamine [J. Org. Chem., 26, 4955 (1961)], was stirred at room temperature for four days. The reaction was filtered and the precipitate dissolved in 500 mL ammonium hydroxide at pH 10.5. This solution was filtered and the solvent removed at reduced pressure. The product was washed in 2×10 mL of water, then with ethanol/ether (1:1) until dry to give 1.65 g of 7-[3-(aminomethyl)-1-pyrrolidinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo -1,8-naphthyridine-3-carboxylic acid, mp 217°-218.5° C. Analysis calculated for C16H19FN4O3.1/2H2O:

Workup

  1. filtrationThe reaction was filtered
  2. dissolutionthe precipitate dissolved in 500 mL ammonium hydroxide at pH 10.5
  3. filtrationThis solution was filtered
  4. customthe solvent removed at reduced pressure
  5. washThe product was washed in 2×10 mL of water
  6. dry with materialwith ethanol/ether (1:1) until dry

Sources & evidence

ORD record
ord-4d4819d42ef0449384565506149a664b
Source dataset
uspto-grants-1994_01
Patent number
US05281612

Reaction notes

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