Hexahydro-1,4-diazepine → HCID 19813641, compound

HRID 467279Notes

Reaction equation

HRID 467279 reaction equation
Cl[C:2]1[CH: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[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([N:19]3[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH:11]=2)[C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8]1)[CH3:13]

Participants

3

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 19813641HCID 19813641, compoundYield 40.2%

Conditions

Temperature
140 °C

Procedure

A mixture of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid [J. Med. Chem., 23, 1358 (1980)] (2.7 g, 10 mmol) and homopiperzine, (5.0 g, 50 mmol) was heated at 140° C. for 51/2 hours. The excess homopiperazine was removed by distillation at 85°-95° C./10 mm Hg. The residue was triturated with water and filtered. The solid collected was dissolved in glacial acetic acid (1.5 mL), water (10 mL) was added, and the pH was adjusted to 8.0 with solid sodium bicarbonate. The resulting precipitate was collected by filtration, washed with water (3×5 mL) and air dried to give the product as a white crystalline solid (1.34 g, 40% yield): mp 196°-198° C.

Workup

  1. customThe excess homopiperazine was removed by distillation at 85°-95° C./10 mm Hg
  2. customThe residue was triturated with water
  3. filtrationfiltered
  4. customThe solid collected
  5. dissolutionwas dissolved in glacial acetic acid (1.5 mL)
  6. additionwater (10 mL) was added
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with water (3×5 mL) and air
  9. customdried

Sources & evidence

ORD record
ord-5412d66051e14b5c86a99301e6629ce7
Source dataset
uspto-grants-1992_10
Patent number
US05159077

Reaction notes

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