Ammonium Chloride → 2,6-Difluoro-9-(1-methylpiperidin-4-YL)-9H-thioxanthen-9-OL

HRID 2083770Notes

Reaction equation

HRID 2083770 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Mg].[F:10][C:11]1[CH:24]=[CH:23][C:22]2[S:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([F:25])[CH:19]=3)[C:14](=[O:26])[C:13]=2[CH:12]=1.[Cl-].[NH4+]>O1CCCC1>[F:10][C:11]1[CH:24]=[CH:23][C:22]2[S:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([F:25])[CH:19]=3)[C:14]([CH:2]3[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]3)([OH:26])[C:13]=2[CH:12]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 203574842,6-Difluoro-9H-thioxanthen-9-one

Product 1

HCID 203574792,6-Difluoro-9-(1-methylpiperidin-4-YL)-9H-thioxanthen-9-OL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The Grignard reagent prepared from 2.7 g. (0.02 mol) of 4-chloro-N-methylpiperidine and 0.5 g. (0.02 mol) of magnesium turnings in tetrahydrofuran is treated with 2.5 g. (0.01 mol) of 2,6-difluorothioxanthone at a rate to maintain slow reflux. The mixture is refluxed for six hours, hydrolyzed with saturated ammonium chloride solution and extracted with ether to yield 2,6-difluoro-9-(1-methyl-4-piperidyl)-thioxanthene-9-ol, m.p. 207°-209° C.

Workup

  1. extractionextracted with ether

Sources & evidence

ORD record
ord-8ef1ec4c11af45f8b00f522d2b3e915a
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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