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

HRID 345499

Reaction equation

HRID 345499 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:16])[CH2:14][CH3:15])=[CH:5][CH:4]=1.[CH2:17]=O.Cl.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]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:16])[CH:14]([CH3:17])[CH2:15][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 212848Pyrrolidine, hydrochloride (1:1)HCID 149942371-(4-Methoxy-5,6,7,8-tetrahydro-1-naphthyl)-1-propanone

Product 1

HCID 140713261-(4-Methoxy-5,6,7,8-tetrahydro-1-naphthyl)-2-methyl-3-pyrrolidino-1-propanoneYield 83.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)-1-propanone (4.37g), paraformaldehyde (1.80g), pyrrolidine hydrochloride (3.23g), and hydrochloric acid (0.2 ml) in isopropyl alcohol (50 ml) was refluxed for 8 hours. 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 and then filtered. The filtrate was evaporated in vacuo to give 1-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)-2-methyl-3-pyrrolidino -1-propanone. (5.06; yield: 83.9%).

Workup

  1. temperaturewas refluxed for 8 hours
  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. filtrationfiltered
  9. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-26c75cddd09e4ce0890f2852628908e7
Source dataset
uspto-grants-1991_10
Patent number
US05057535

Linked notes

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