Triethylamine → HCID 13146122, compound

HRID 2296374Notes

Reaction equation

HRID 2296374 reaction equation
Cl.[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:12]=2[F:14])[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]1)[CH3:3].C(N(CC)CC)C.[N+:33]([C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1)([O-:35])=[O:34]>CN(C)C=O>[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]3[CH2:16][CH2:17][N:18]([CH2:40][C:39]4[CH:42]=[CH:43][C:36]([N+:33]([O-:35])=[O:34])=[CH:37][CH:38]=4)[CH2:19][CH2:20]3)[C:12]=2[F:14])[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]1)[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 12770893HCID 12770893, compound

Product 1

HCID 13146122HCID 13146122, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid hydrochloride (6.7 g), triethylamine (5.45 g), p-nitrobenzylbromide (5.8 g) and dimethylformamide (200 ml) was stirred at 90° C. for 10.5 hrs. The solvent was evaporated off and the residue was treated with water. The solid was filtered, washed with water, dried, and recrystallized from a mixture of dimethylformamide and ethanol to give 6.9 g of 1-ethyl-6,8-difluoro-1,4-dihydro-7-[4-(p-nitrobenzyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid. mp: 241°-242° C.

Workup

  1. customThe solvent was evaporated off
  2. additionthe residue was treated with water
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried
  6. customrecrystallized from a mixture of dimethylformamide and ethanol

Sources & evidence

ORD record
ord-f039af4499e34091a0f80f3ed6177c0f
Source dataset
uspto-grants-1984_01
Patent number
US04429127

Reaction notes

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