Hydrochloric Acid → 1-(4-Methoxy-5,6,7,8-tetrahydro-1-naphthyl)-2-ethyl-3-pyrrolidino-1-propanone

HRID 345497

Reaction equation

HRID 345497 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])[CH2:14][CH2:15][CH3:16])=[CH:5][CH:4]=1.[CH2:18]=O.Cl.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.Cl>C(O)(C)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])[CH:14]([CH2:15][CH3:16])[CH2:18][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 212848Pyrrolidine, hydrochloride (1:1)HCID 149942361-(4-Methoxy-5,6,7,8-tetrahydro-1-naphthyl)-1-butanone

Product 1

HCID 140713341-(4-Methoxy-5,6,7,8-tetrahydro-1-naphthyl)-2-ethyl-3-pyrrolidino-1-propanoneYield 62.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)-1-butanone (2.50g), paraformaldehyde (0.42g), pyrrolidine hydrochloride (1.51g), and hydrochloric acid (0.2 ml) in isopropyl alcohol (7 ml) was refluxed for 15 hrs. The reaction mixture was evaporated in vacuo to give the residue. The residue was partitioned into water and ethyl ether. The aqueous layer, was extracted, neutralized with ammonia water, and then extracted with ethyl ether. The organic layer was dried over anhydrous magnesium sulfate. The mixture was filtered and the filtrate was evaporated in vacuo to give 1-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)-2-ethyl-3-pyrrolidino-1-propanone (2.13 g, Yield: 62.8 %) as an oil.

Workup

  1. temperaturewas refluxed for 15 hrs
  2. customThe reaction mixture was evaporated in vacuo
  3. customto give the residue
  4. customThe residue was partitioned into water and ethyl ether
  5. extractionThe aqueous layer, was extracted
  6. extractionextracted with ethyl ether
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationThe mixture was filtered
  9. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c8f0fe61614e40adb00ef055c2d4b977
Source dataset
uspto-grants-1991_10
Patent number
US05057535

Linked notes

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