Dimethylformamide → HCID 15622954, compound

HRID 2108153Notes

Reaction equation

HRID 2108153 reaction equation
[C:1]1([CH:7]2[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].Cl[C:21]([O:29][CH2:30][CH:31]([CH3:33])[CH3:32])(C)[CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.[CH3:34]N(C)C=O>O>[CH3:33][CH:31]([CH3:32])[CH2:30][O:29][CH2:21][CH:22]([N:23]1[CH2:24][CH2:25][CH2:26][CH2:27]1)[CH2:34][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 1177592-Phenyl-2,3-dihydro-1H-indoleHCID 23045582HCID 23045582, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15622954HCID 15622954, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4 g. 2-Phenylindoline are dissolved in 25 ml. dimethylformamide and the solution mixed with 1.2 g. sodium hydride (50% suspension in oil). The reaction mixture is heated, while stirring, to 80° C. until the evolution of hydrogen is finished. Thereafter, a solution of 4.5 g. 1-[2-chloro-2-(2-methylpropoxy)-propyl]pyrrolidine in 25 ml. dimethylformamide is added dropwise thereto in the course of 15 minutes and stirring continued for 3 hours at 80° C. The reaction mixture is cooled, mixed with water and extracted with methylene chloride. The methylene chloride phase is washed with water, dried over anhydrous sodium sulphate and evaporated. For purification, the residue is chromatographed on a silica gel column (elution agent: toluene/10% ethyl acetate). After evporation of the appropriate column fractions, there are obtained 3.5 g. of the title compound in the form of an oily product.

Workup

  1. temperatureThe reaction mixture is heated
  2. waitcontinued for 3 hours at 80° C
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with methylene chloride
  5. washThe methylene chloride phase is washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated
  8. customFor purification
  9. customthe residue is chromatographed on a silica gel column (elution agent: toluene/10% ethyl acetate)
  10. customAfter evporation of the appropriate column fractions, there are obtained 3.5 g

Sources & evidence

ORD record
ord-d49bbb6b723941928cae58d02ff63f4e
Source dataset
uspto-grants-1990_06
Patent number
US04937337

Reaction notes

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