Diethyl Ether → HCID 14676872, compound

HRID 1165580Notes

Reaction equation

HRID 1165580 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[C:10]2[NH:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:9]=2[S:8][CH2:7][CH2:6]1)[CH3:3].[H-].[Na+].[CH:20](I)([CH3:22])[CH3:21].CCOCC>CN(C)C=O>[CH3:3][N:2]([CH2:4][CH:5]1[C:10]2[N:11]([CH:20]([CH3:22])[CH3:21])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:9]=2[S:8][CH2:7][CH2:6]1)[CH3:1]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 12803597HCID 12803597, compound

Product 1

HCID 14676872HCID 14676872, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-dimethylaminomethyl-2,3,4,5-tetrahydrothiopyrano[3,2-b]indole (1.00 g) in dry dimethylformamide (25 ml) is mixed with 50% sodium hydride (293 mg) under stirring and the mixture is allowed to stand at 40° C. for 1 hour. Then, the reaction mixture is mixed with a solution of isopropyl iodide (1.63 g) in dimethylformamide (2 ml) and kept at 40° C. for 2 hours and further for 20 hours after addition of the reagent. The reaction mixture is mixed with ether and ice water successively at under 5° C. and the ether layer is separated. The aqueous layer is further extracted with ether. The combined ether layers are extracted with a dilute hydrochloric acid solution. The extract is made alkaline and extracted with methylene chloride. The extract is washed with water, dried and evaporated to give the title compound (910 mg) as an oil: Yield 77.8%.

Workup

  1. waitkept at 40° C. for 2 hours and further for 20 hours
  2. additionafter addition of the reagent
  3. customthe ether layer is separated
  4. extractionThe aqueous layer is further extracted with ether
  5. extractionThe combined ether layers are extracted with a dilute hydrochloric acid solution
  6. extractionextracted with methylene chloride
  7. washThe extract is washed with water
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-8c87e514229c4cde8a08f168669d11bf
Source dataset
uspto-grants-1990_03
Patent number
US04910318

Reaction notes

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