Ammonium Chloride → HCID 12815923, compound

HRID 1388534Notes

Reaction equation

HRID 1388534 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:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][C:18]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:19]=1[CH:20]=[O:21].[Cl-].[NH4+]>O1CCCC1>[CH3:8][N:5]1[CH2:6][CH2:7][CH:2]([CH:20]([OH:21])[C:19]2[CH:22]=[C:23]([C:26]([F:27])([F:28])[F:29])[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])[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 12815915HCID 12815915, compound

Product 1

HCID 12815923HCID 12815923, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the Grignard reagent is prepared by a reaction of 12.0 g 4-chloro-1-methylpiperidine with 2.3 g of magnesium in 70 ml of tetrahydrofuran and is treated for 10 minutes with a solution of 17.4 g 2-(2-fluorophenylthio)-5-trifluoromethylbenzaldehyde in 40 ml of tetrahydrofuran added dropwise. The mixture is refluxed for 4 hours and after cooling, decomposed with a 20% ammonium chloride solution and extracted with benzene. The extract is dried with potassium carbonate and evaporated. There are obtained 23.2 g (100%) crude oily α-(1-methyl-4-piperidyl)-2-(2-fluorophenylthio)-5-trifluoromethylbenzyl alcohol which is used in this state for the final reaction.

Workup

  1. additionadded dropwise
  2. temperatureThe mixture is refluxed for 4 hours
  3. extractionextracted with benzene
  4. dry with materialThe extract is dried with potassium carbonate
  5. customevaporated

Sources & evidence

ORD record
ord-4ce1b743796e43a8b342e519d5c86ef1
Source dataset
uspto-grants-1984_02
Patent number
US04431808

Reaction notes

Loading…