4-chloro-N-methylpiperidine → HCID 23329078, compound

HRID 225139Notes

Reaction equation

HRID 225139 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Mg].[CH3:10][S:11][C:12]1[CH:25]=[CH:24][C:23]2[S:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:26])[CH:20]=3)[C:15](=[O:27])[C:14]=2[CH:13]=1>O1CCCC1>[CH3:10][S:11][C:12]1[CH:25]=[CH:24][C:23]2[S:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:26])[CH:20]=3)[C:15]([CH:2]3[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]3)([OH:27])[C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 23329082HCID 23329082, compound

Product 1

HCID 23329078HCID 23329078, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a Grignard-solution prepared from 130 grams of 4-chloro-1-methylpiperidine and 24 grams of magnesium turnings in 500 milliliters of dry tetrahydrofuran was added 174 grams of 2-methylthio-6-fluoro-thioxanthene-9-one in portions while stirring and cooling in an ice-salt mixture. The reaction temperature was kept below 10 degrees Centigrade. The cooling bath was then removed and the reaction mixture was stirred at 35-40 degrees Centigrade for 1.5 hours. The reaction mixture was then poured into a mixture of ice, water and ammonium chloride. The crystalline precipitate which was obtained upon cooling was sucked off, washed with water and dissolved in 10% aqueous acetic acid. The solution was treated with charcoal, extracted three times with 100 milliliters of ether and then made alkaline with 10 N sodium hydroxide solution. After cooling the precipitated base was sucked off, washed with water, suspended in 100 milliliters of acetone, filtered, again suspended in 100 milliliters of acetone, and then filtered and dried to yield 142 grams of 2-methylthio-6-fluoro-9-(1-methyl-4-piperidyl)-thioxanthen-9-ol which melted at 180-189 degrees Centigrade. The analytically pure compound melts at 192-195 degrees Centigrade after recrystallization from diethylether.

Workup

  1. customwas kept below 10 degrees Centigrade
  2. customThe cooling bath was then removed
  3. stirringthe reaction mixture was stirred at 35-40 degrees Centigrade for 1.5 hours
  4. additionThe reaction mixture was then poured into a mixture of ice, water and ammonium chloride
  5. customThe crystalline precipitate which was obtained
  6. temperatureupon cooling
  7. washwashed with water
  8. dissolutiondissolved in 10% aqueous acetic acid
  9. additionThe solution was treated with charcoal
  10. extractionextracted three times with 100 milliliters of ether
  11. temperatureAfter cooling the precipitated base
  12. washwashed with water
  13. filtrationfiltered
  14. filtrationfiltered
  15. customdried

Sources & evidence

ORD record
ord-b1c84b0f3842414fa7a28928ee31a016
Source dataset
uspto-grants-1980_11
Patent number
US04235916

Reaction notes

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