Triethylamine → (S)-7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 729064Notes

Reaction equation

HRID 729064 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[CH:8]1([N:11]2[C:20]3[C:15](=[CH:16][C:17]([F:23])=[C:18](F)[C:19]=3[F:21])[C:14](=[O:24])[C:13]([C:25]([OH:27])=[O:26])=[CH:12]2)[CH2:10][CH2:9]1.C(N(CC)CC)C>C(#N)C>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:18]2[C:19]([F:21])=[C:20]3[C:15]([C:14](=[O:24])[C:13]([C:25]([OH:27])=[O:26])=[CH:12][N:11]3[CH:8]3[CH2:10][CH2:9]3)=[CH:16][C:17]=2[F:23])[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 855017(S)-piperidin-3-amine

Product 1

HCID 11089787(S)-7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 79.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of (S)-3-aminopiperidine (4.0 g) obtained as described in the step (c) above 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid(11.4 g) and triethylamine (8.4 g) in acetonitrile (250 ml) was refluxed for 3 hours with stirring. Then the mixture was cooled down and filtrationof the precipitated powder followed by treatment with a mixture of ethanol (550 ml) and water (250 ml) gave (S)-7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (11.6 g) as colorless needles. m.p. 247.8° C. (decomposition).

Workup

  1. customobtained
  2. temperaturewas refluxed for 3 hours
  3. temperatureThen the mixture was cooled down
  4. filtrationfiltrationof the precipitated powder
  5. additionfollowed by treatment with a mixture of ethanol (550 ml) and water (250 ml)

Sources & evidence

ORD record
ord-8853347b3393489aab5ae2f9facf1c59
Source dataset
uspto-grants-1991_09
Patent number
US05051509

Reaction notes

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