Potassium Iodide → HCID 14071333, compound

HRID 345501Notes

Reaction equation

HRID 345501 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([C:13](=[O:18])[CH2:14][CH2:15][CH2:16]Cl)=[CH:5][CH:4]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)C>[CH3:1][O:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([C:13](=[O:18])[CH2:14][CH2:15][CH2:16][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 14994238HCID 14994238, compound

Product 1

HCID 14071333HCID 14071333, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)-4-chloro-1-butanone (4.0g), pyrrolidine (4.27g), potassium iodide (0.3g) and potassium carbonate (2.0g) in absolute N,N-dimethylformamide (30 ml) was stirred at 60° C. for 10 hours. The reaction mixture was filtered and then the filtrate was partitioned into water and ethyl acetate. The organic layer was extracted, washed with water and then dried over anhydrous magnesium sulfate. The mixture was filtered and the filtrate was evaporated in vacuo to give the residue. The residue was dissolved in ethyl ether. The ethyl ether solution was extracted with 1N hydrochloric acid. The aqueous layer was neutralized with ammonia water and then extracted with ethyl ether. The ethyl ether was dried over anhydrous magnesium sulfate. The solution was filtered and the filtrate was evaporated in vacuo to give 1-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)-4-pyrrolidino-1-butanone (3.7 g; yield: 82%) as an oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was partitioned into water and ethyl acetate
  3. extractionThe organic layer was extracted
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe mixture was filtered
  7. customthe filtrate was evaporated in vacuo
  8. customto give the residue
  9. extractionThe ethyl ether solution was extracted with 1N hydrochloric acid
  10. extractionextracted with ethyl ether
  11. dry with materialThe ethyl ether was dried over anhydrous magnesium sulfate
  12. filtrationThe solution was filtered
  13. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-a5c9fbe8fa1a4be19a5dc6efeee5089d
Source dataset
uspto-grants-1991_10
Patent number
US05057535

Reaction notes

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