Benzoyl chloride, 3,4-dichloro- → HCID 14032554, compound
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][N:9]=2)[CH2:4][CH2:3]1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[Cl:27])[C:21](Cl)=[O:22]>CCOCC>[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[Cl:27])[C:21]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[N:9]1)=[O:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 3.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole and 8 ml of 3,4-dichlorobenzoyl chloride was heated at 100° C. in a steam bath for 4 hrs. After the reaction mixture cooled to ambient temperature, ether was added and the salt was collected. The salt was mixed with water and ammonium hydroxide solution was added until the mixture was basic. The mixture was warmed on the steam bath for about 5 mins, cooled and extracted with dichloromethane. Evaporation of the dichloromethane in vacuo provided the free base. The base was recrystallized from methanol-trichloromethane (with concentration of the mother liquor) to yield 3.0 g (57%) of product, mp 187°-189° C.
Workup
- temperatureAfter the reaction mixture cooled to ambient temperature
- customthe salt was collected
- additionThe salt was mixed with water and ammonium hydroxide solution
- additionwas added until the mixture
- temperatureThe mixture was warmed on the steam bath for about 5 mins
- temperaturecooled
- extractionextracted with dichloromethane
- customEvaporation of the dichloromethane in vacuo
- customprovided the free base
- customThe base was recrystallized from methanol-trichloromethane (with concentration of the mother liquor)
Sources & evidence
- ORD record
- ord-56aab486c79348f0a0af325e14197314
- Source dataset
- uspto-grants-1990_06
- Patent number
- US04933460
Reaction notes
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