Ethanol → HCID 18467278, compound

HRID 1900462Notes

Reaction equation

HRID 1900462 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 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-6e8766ea30d740d1bc6a863431485f47
Source dataset
uspto-grants-1996_11
Patent number
US05574032

Reaction notes

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