Ethanol → HCID 18467278, compound

HRID 611929Notes

Reaction equation

HRID 611929 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

Conditions

Temperature
175 °C

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 175° C. 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. stirringThe compound was stirred
  5. customfor 1 hour
  6. customat ambient temperature
  7. customovernight
  8. customThe solid was collected
  9. customdried
  10. customto afford 6.9 g
  11. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-8cabcecdf5604b88bb5803de23c68a83
Source dataset
uspto-grants-1999_12
Patent number
US06001834

Reaction notes

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