1-Butanol → HCID 15057453, compound

HRID 1032290Notes

Reaction equation

HRID 1032290 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=S)[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.C(O)CCC.O.[NH2:30][NH2:31].C(=O)([O-])[O-].[Na+].[Na+]>CC1C=CC=CC=1.O.C(O)(=O)C>[F:8][C:6]1[CH:7]=[C:2]2[C:3]([C:9]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:12][CH2:11]3)=[N:30][NH:31]2)=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 2631-ButanolHCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 150574521-[(2,4-Difluorophenyl)thioxomethyl]-4-(phenylmethyl)piperazine

Product 1

HCID 15057453HCID 15057453, compoundYield 32.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 40 parts of 1-[(2,4-difluorophenyl)thioxomethyl]-4-(phenylmethyl)piperazine, 144 parts of 1-butanol, 13 parts of hydrazine monohydrate and 24 parts of acetic acid was stirred overnight at reflux temperature. After cooling, 50 parts of sodium carbonate were added and stirring was continued for 3 hours at reflux temperature. The reaction mixture was cooled until room temperature and water and methylbenzene were added. After stirring for 15 minutes, the separated organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (92:8 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 12 parts (32.2%) of 6-fluoro-3-[4-(phenylmethyl)piperazinyl]-1H-indazole; mp. 162.0° C. (int. 7).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. stirringstirring
  4. waitwas continued for 3 hours
  5. temperatureat reflux temperature
  6. stirringAfter stirring for 15 minutes
  7. customthe separated organic layer was dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (92:8 by volume) as eluent
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated
  14. customThe residue was crystallized from acetonitrile
  15. filtrationThe product was filtered off
  16. customdried

Sources & evidence

ORD record
ord-f03e1b21a40f4ba9a696e02b3b109258
Source dataset
uspto-grants-1990_09
Patent number
US04957916

Reaction notes

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