Methyl iodide → HCID 23463959, compound

HRID 444534Notes

Reaction equation

HRID 444534 reaction equation
CO[C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11]CCNCCCCNCCCN)[CH:6]=[CH:5][C:4]=1O.[CH2:25]([N:28](C1NC=C2CCCCC=12)[CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27].[CH3:41]C(N(C)C)=O.CC(C)([O-])C.[K+].CI>O>[CH3:41][N:10]1[CH:11]=[C:8]2[C:7]([CH2:6][CH2:5][CH:4]([N:28]([CH2:29][CH2:30][CH3:31])[CH2:25][CH2:26][CH3:27])[CH2:3]2)=[CH:9]1

Participants

6

Reactant 4

HCID 6328Methyl iodide2×HCID 31374Dimethylacetamide2×HCID 23665647Potassium tert-butoxideHCID 131712198HCID 131712198, compound

Product 1

HCID 23463959HCID 23463959, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 millimoles (680 mg) of dl-5-di(n-propyl)amino 4,5,6,7-tetrahydro-2H-benzo[c]pyrrole were dissolved in 75 ml. of dimethylacetamide (DMA). 10 millimoles (1.1 g) potassium tertiary-butoxide were added and the resulting mixture stirred for 20 minutes under nitrogen. Next, a solution of 2.1 millimoles of methyl iodide (0.13 ml) in 5 ml. of DMA was added in dropwise fashion. The resulting reaction mixture was stirred at ambient temperature for 5 hours at which time an additional 0.13 ml of methyl iodide was added and the subsequent mixture stirred for an additional 3.5 hours. The reaction mixture was then diluted with water and the aqueous layer extracted with ethyl acetate. The ethyl acetate layer was separated and washed with water followed by saturated aqueous sodium chloride. The ethyl acetate layer was then dried and the ethyl acetate removed therefrom by evaporation. An ether solution of the resulting residue was chromatographed over 35 g. of Florisil using ether as the eluant. Fractions shown by TLC to contain dl-2-methyl-5-di-n-propylamino- 4,5,6,7-2H-benzo[c]pyrrole were combined and the solvent removed therefrom in vacuo. NMR of the residue thus obtained indicated that the dl-2-methyl-5-di-n-propylamino-4,5,6,7-2H-benzo[c]pyrrole had been prepared.

Workup

  1. customThe resulting reaction mixture
  2. additionwas added
  3. stirringthe subsequent mixture stirred for an additional 3.5 hours
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. customThe ethyl acetate layer was separated
  6. washwashed with water
  7. dry with materialThe ethyl acetate layer was then dried
  8. customthe ethyl acetate removed
  9. customby evaporation
  10. customAn ether solution of the resulting residue was chromatographed over 35 g
  11. customthe solvent removed
  12. customNMR of the residue thus obtained
  13. customhad been prepared

Sources & evidence

ORD record
ord-3fcaa85371654afc858e7c0f8d656385
Source dataset
uspto-grants-1981_04
Patent number
US04264622

Reaction notes

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