1-Fluoro-2-nitrobenzene → 6-Chloro-1'-methyl-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25].C(=O)(O)[O-].[Na+]>>[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:24]([O-:26])=[O:25])[CH2:9][C:10]3([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1Participants
4
Procedure
A mixture of 2.4 g of 6-chloro-1'-methylspiro[indoline-3,4'-piperidine], Example 23b, 5.4 g of 2-fluoronitrobenzene and 1.0 g of sodium bicarbonate is stirred at 160°-165° C. under nitrogen, for 16 hours. Thereafter, the mixture is permitted to cool before sequentially being quenched with water and extracted thrice with ether. The combined ether extracts are shaken with a large excess of 1 N hydrochloric acid. The acidified layer is basified providing a reddish oil which upon drying over magnesium sulfate and then cooling leaves an orange solid. The solid is recrystallized from an etherpentane mixture to provide prisms, mp 130°-131° C. of 6-chloro-1'-methyl-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine].
Workup
- temperatureto cool
- custombefore sequentially being quenched with water
- extractionextracted thrice with ether
- stirringThe combined ether extracts are shaken with a large excess of 1 N hydrochloric acid
- customThe acidified layer is basified providing a reddish oil which
- dry with materialupon drying over magnesium sulfate
- temperaturecooling
- customleaves an orange solid
- customThe solid is recrystallized from an etherpentane mixture
Sources & evidence
- ORD record
- ord-80072128ec374262bd9e32eb86112d59
- Source dataset
- uspto-grants-1983_04
- Patent number
- US04379932
Reaction notes
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