Ammonium Chloride → HCID 12815922, compound

HRID 1388532Notes

Reaction equation

HRID 1388532 reaction equation
[Mg].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6](Cl)[CH2:5][CH2:4]1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][C:18]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:19]=1[CH:20]=[O:21].[Cl-].[NH4+]>O1CCCC1>[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([CH:20]([OH:21])[C:19]2[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:18]=2[S:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[F:10])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 12815914HCID 12815914, compound

Product 1

HCID 12815922HCID 12815922, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the Grignard reagent is prepared by reaction of 2.5 g of magnesium with 13.35 g of 1-methyl-4-chloropiperidine (reference above) in 80 ml of tetrahydrofuran in the usual manner. Over 15 minutes with stirring, a solution of 18.2 g of 2-(2-fluorophenylthio)-5-methoxybenzaldehyde in 40 ml tetrahydrofuran is added dropwise and the mixture refluxed for 4 hours. After cooling, it is decomposed with 20% ammonium chloride solution and extracted with benzene. The extract is dried with potassium carbonate and evaporated. There are obtained 23.7 g (100%) crude oily α-(1-methyl-4-piperidyl)-2-(2-fluorophenylthio)-5-methoxybenzyl alcohol which is used for further work without purification.

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. temperatureAfter cooling
  3. extractionextracted with benzene
  4. dry with materialThe extract is dried with potassium carbonate
  5. customevaporated

Sources & evidence

ORD record
ord-ef0da2ec374247c38e723c0266c4ce1e
Source dataset
uspto-grants-1984_02
Patent number
US04431808

Reaction notes

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