Methyl iodide → HCID 12917667, compound

HRID 1277774Notes

Reaction equation

HRID 1277774 reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:10]([Cl:20])[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:23]I.[Cl-].[NH4+]>CN(C)C=O>[CH3:1][S:2][C:3]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:10]([Cl:20])[CH:9]=1)([CH3:23])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23453440HCID 23453440, compound

Product 1

HCID 12917667HCID 12917667, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl α-methylthio(3-chloro-4-piperidinophenyl)acetate (2.524 g) was dissolved in 15 ml of N,N-dimethylformamide, and under ice cooling, 420 mg of sodium hydride (65% content) was added. The mixture was stirred for 15 minutes, and then 3.5 ml of methyl iodide was added. The mixture was stirred for 2 minutes under ice cooling, and then for 1 hour and 15 minutes at room temperature. Then 60 ml of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted twice with 25 ml of methylene chloride. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford a brown oily product. The oily product was chromatographed on a column of Florisil using n-hexane-benzene as an eluent to afford 2.012 g (76.2%) of methyl α-methylthio-α-(3-chloro-4-piperidinophenyl)propionate. On standing overnight, the product crystallized.

Workup

  1. stirringThe mixture was stirred for 2 minutes under ice cooling
  2. waitfor 1 hour
  3. custom15 minutes
  4. customat room temperature
  5. extractionthe mixture was extracted twice with 25 ml of methylene chloride
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto afford a brown oily product
  9. customThe oily product was chromatographed on a column of Florisil

Sources & evidence

ORD record
ord-5c0d758905dd40ee90ee92a24dea4a2a
Source dataset
uspto-grants-1981_07
Patent number
US04278802

Reaction notes

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