Iodoethane → 1-diphenylmethyl-3-methyl-3-[N-(ethyl)trifluoroacetylaminomethyl]azetidine

HRID 1461113Notes

Reaction equation

HRID 1461113 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:10]2[CH2:13][C:12]([CH3:22])([CH2:14][NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:29](I)[CH3:30]>O1CCOCC1.CN(C)C=O>[C:23]1([CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:10]2[CH2:13][C:12]([CH3:22])([CH2:14][N:15]([C:16](=[O:21])[C:17]([F:18])([F:19])[F:20])[CH2:29][CH3:30])[CH2:11]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 104738161-Diphenylmethyl-3-methyl-3-trifluoroacetylaminomethylazetidine

Product 1

HCID 100459041-diphenylmethyl-3-methyl-3-[N-(ethyl)trifluoroacetylaminomethyl]azetidineYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

0.16 g (3.6 mmol) of 55% strength sodium hydride is added to a solution of 1.3 g (3.6 mmol) of 1-diphenylmethyl-3-methyl-3-trifluoroacetylaminomethylazetidine in 40 ml of dioxane and 10 ml of dimethylformamide, and the mixture is stirred for two hours at 60°-70° C. The solution is cooled to room temperature, 0.73 g (4.6 mmol) of ethyl iodide is added, the mixture is stirred for 4 hours at 70° C. and evaporated to dryness, the residue is dissolved with chloroform, the organic phase is washed with water, dried with anhydrous sodium sulphate and evaporated and 1.1 g (79%) of 1-diphenylmethyl-3-methyl-3-[N-(ethyl)trifluoroacetylaminomethyl]azetidine are obtained. This compound is dissolved in ethanol, and ethyl ether saturated with hydrochloric acid is added. The product is allowed to crystallize and is filtered off, and 1-diphenylmethyl-3-methyl-3-[N-(ethyl)trifluoroacetylaminomethyl]azetidine hydrochloride, melting point 191°-4° C., is obtained.

Workup

  1. stirringthe mixture is stirred for 4 hours at 70° C.
  2. customevaporated to dryness
  3. dissolutionthe residue is dissolved with chloroform
  4. washthe organic phase is washed with water
  5. dry with materialdried with anhydrous sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-acd5a1eeba2f497292bf4713cf39bcd3
Source dataset
uspto-grants-1991_12
Patent number
US05073646

Reaction notes

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