N,N-Dimethylpiperidin-4-amine → HCID 12770916, compound

HRID 434572Notes

Reaction equation

HRID 434572 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[CH3:20][N:21]([CH3:28])[CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>N1C=CC=CC=1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:25]3[CH2:26][CH2:27][CH:22]([N:21]([CH3:28])[CH3:20])[CH2:23][CH2:24]3)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 417391N,N-Dimethylpiperidin-4-amineHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 12770916HCID 12770916, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.43 g), 4-dimethylaminopiperidine (2.1 g), and pyridine (3 ml) was refluxed for 6 hours. The mixture was evaporated to dryness. The residue was treated with water and extracted with dichloromethane. The organic layer was washed with water, dried, and evaporated. The solid was recrystallized from ethyl acetate and gave 1-ethyl-6,8-difluoro-1,4-dihydro-7-(4-dimethylamino-1-piperidinyl)-4-oxoquinoline-3-carboxylic acid (0.22 g), mp 210°-211° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe mixture was evaporated to dryness
  3. additionThe residue was treated with water
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water
  6. customdried
  7. customevaporated
  8. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d2bf2a5012bc4dc299784890bc5d00a5
Source dataset
uspto-grants-1983_08
Patent number
US04398029

Reaction notes

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