Pyrrolidine → HCID 14994240, compound

HRID 345502Notes

Reaction equation

HRID 345502 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:17])[CH:14]=[CH:15][CH3:16])=[CH:5][CH:4]=1.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)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:17])[CH2:14][CH:15]([CH3:16])[N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 53977036HCID 53977036, compound

Product 1

HCID 14994240HCID 14994240, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)-2-butene-1-one (3.0 g) and pyrrolidine (1.85 g) in ethanol (100 ml) was stirred for 3 hours at room temperature. The mixture was evaporated in vacuo to give the residue. The residue was partitioned into water and ethyl ether The ethyl ether was washed with water. The organic layer was extracted with 2N 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 and then filtered. The filtrate was evaporated in vacuo to give 1-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)-3-methyl-3-pyrrolidino-1-propanone (2.31 g, Yield: 53.6%) as an oil.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto give the residue
  3. customThe residue was partitioned into water and ethyl ether The ethyl ether
  4. washwas washed with water
  5. extractionThe organic layer was extracted with 2N hydrochloric acid
  6. extractionextracted with ethyl ether
  7. dry with materialThe ethyl ether was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-169abc51bd84481b9788ae8997970a4d
Source dataset
uspto-grants-1991_10
Patent number
US05057535

Reaction notes

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