Choline, hydroxide → Choline 7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate

HRID 1266155Notes

Reaction equation

HRID 1266155 reaction equation
[OH-].[OH:2][CH2:3][CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6].[F:9][C:10]1[C:28]([N:29]2[CH2:34][CH2:33][N:32]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[CH2:31][CH2:30]2)=[CH:27][C:13]2=[N:14][C:15]3[N:16]([CH3:26])[CH:17]=[C:18]([C:23]([OH:25])=[O:24])[C:19](=[O:22])[C:20]=3[CH:21]=[C:12]2[CH:11]=1>CO>[OH:2][CH2:3][CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6].[F:9][C:10]1[C:28]([N:29]2[CH2:30][CH2:31][N:32]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[CH2:33][CH2:34]2)=[CH:27][C:13]2=[N:14][C:15]3[N:16]([CH3:26])[CH:17]=[C:18]([C:23]([O-:25])=[O:24])[C:19](=[O:22])[C:20]=3[CH:21]=[C:12]2[CH:11]=1

Participants

4

Reactant 2

HCID 31255Choline, hydroxideHCID 484065RP60556A

Product 1

HCID 9959323Choline 7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

7.6 cm3 of a 45% solution of choline hydroxide in methanol were added to a suspension of 7.6 g of 7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid in 75 cm3 of methanol. The reaction mixture was stirred for approximately 2 hours at approximately 25° C. The solution was filtered in order to remove a slight insoluble material and was concentrated at approximately 50° C. on a rotary evaporator at approximately 20 kPa. The residual solid was recrystallized from 70 cm3 of 2-propanol and 30 cm3 of methanol. The crystals were filtered off with 10 cm3 of 2-propanol on each occasion and dried in an oven at 100° C. at 10 kPa. 7.4 g of choline 7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate were obtained in the form of a yellow solid melting at about 285-90° C.

Workup

  1. filtrationThe solution was filtered in order
  2. customto remove a slight insoluble material
  3. concentrationwas concentrated at approximately 50° C. on a rotary evaporator at approximately 20 kPa
  4. customThe residual solid was recrystallized from 70 cm3 of 2-propanol and 30 cm3 of methanol
  5. filtrationThe crystals were filtered off with 10 cm3 of 2-propanol on each occasion
  6. customdried in an oven at 100° C. at 10 kPa

Sources & evidence

ORD record
ord-23f5f136103245198b3b7b3d45bbac40
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

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