Ammonium Chloride → 3-Fluoro-9-(1-methylpiperidin-4-yl)-9H-thioxanthen-9-ol

HRID 2083763Notes

Reaction equation

HRID 2083763 reaction equation
[Mg].Cl[CH:3]1[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.[F:10][C:11]1[CH:12]=[CH:13][C:14]2[C:15](=[O:25])[C:16]3[C:21]([S:22][C:23]=2[CH:24]=1)=[CH:20][CH:19]=[CH:18][CH:17]=3.[Cl-].[NH4+]>O1CCCC1>[F:10][C:11]1[CH:12]=[CH:13][C:14]2[C:15]([CH:3]3[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]3)([OH:25])[C:16]3[C:21]([S:22][C:23]=2[CH:24]=1)=[CH:20][CH:19]=[CH:18][CH:17]=3

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 217304583-Fluoro-9H-thioxanthen-9-one

Product 1

HCID 203575253-Fluoro-9-(1-methylpiperidin-4-yl)-9H-thioxanthen-9-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The Grignard reagent prepared from 0.62 g. of magnesium turnings and 3.5 g. of 4-chloro-N-methylpiperidine in tetrahydrofuran is treated with a solution of 3-fluoro-9-thioxanthone (3.0 g.) in 50 ml. of tetrahydrofuran. The mixture is refluxed for four hours, cooled, treated with saturated ammonium chloride solution and extracted with ether. The ether extract is washed with water, dried and concentrated to give 3-fluoro-9-(1-methyl-4-piperidyl)-thioxanthene-9-ol, m.p. 120°-130° C.

Workup

  1. temperatureThe mixture is refluxed for four hours
  2. temperaturecooled
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washis washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ea2a40de98704208870f2e60807f27b1
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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