Ethanol → HCID 18467278, compound

HRID 2229707Notes

Reaction equation

HRID 2229707 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]4[C:27](=[O:28])[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:20]4=[O:29])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[C:30]([Cl:38])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O)C>CCOCC>[ClH:38].[C:30]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=2)[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]3[C:27](=[O:28])[C:26]4=[CH:25][CH:24]=[CH:23][CH:22]=[C:21]4[C:20]3=[O:29])[CH2:13][CH2:12]2)=[N:7]1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7412Benzoyl chlorideHCID 18467209N-[2-[4-(6-fluoro1H-indazol-3-yl)-1-piperazinyl]ethyl]phthalimide

Product 1

HCID 18467278HCID 18467278, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-[2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]ethyl]-1H-isoindol-1,3-(2H)-dione (6.0 g, 15 mmol) and benzoyl chloride (25 ml) was stirred at 175C. under N2 for 2.0 hours. The reaction was cooled and diluted with anhydrous Et2O and the resultant hydrochloride salt was collected to yield 7.2 g. The compound was stirred in boiling absolute ethanol (300 ml) for 1 hour and then at ambient temperature overnight. The solid was collected and dried to afford 6.9 g. Recrystallization from MeOH gave 3.9 g of a light grey solid, m.p. 257-260° C.

Workup

  1. temperatureThe reaction was cooled
  2. customthe resultant hydrochloride salt was collected
  3. customto yield 7.2 g
  4. customfor 1 hour
  5. customat ambient temperature
  6. customovernight
  7. customThe solid was collected
  8. customdried
  9. customto afford 6.9 g
  10. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-c5a4f8a7b3ed42af994e94ee8d22dcae
Source dataset
uspto-grants-2002_07
Patent number
US06420390B1

Reaction notes

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