Acetic Acid → HCID 18652063, compound

HRID 249458Notes

Reaction equation

HRID 249458 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=O)[CH:8]2[CH3:13].C(O)(=O)C.[CH:19]1([CH2:22][NH2:23])[CH2:21][CH2:20]1>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C@H:7]([NH:23][CH2:22][CH:19]1[CH2:21][CH2:20]1)[C@@H:8]2[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 75646CyclopropanemethanamineHCID 2603915-methoxy-1-methyl-3,4-dihydronaphthalen-2(1h)-one

Product 1

HCID 18652063HCID 18652063, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-methoxy-1-methyl-2-tetralone (2.0 g) in absolute ethanol (50 ml) are added acetic acid (1.9 g), cyclopropylmethylamine (2.0 g) and 4 Å molecular sieves. The mixture is heated in a closed flask at 80° C. for one hour. The molecular sieves are filtered off and the solution is hydrogenated (PtO2) at atmospheric pressure. The catalyst is filtered off (Celite) and the volatiles are evaporated. Dilute hydrochloric acid (50 ml) is added to the solid residue. The resulting acidic solution is washed with ether, made basic 5% sodium hydroxide and extracted twice with ether. The ether extracts are combined, dried (sodium sulfate) and evaporated. The resulting crude base is eluted through an alumina column with ether-light petroleum (1:4).

Workup

  1. filtrationThe molecular sieves are filtered off
  2. filtrationThe catalyst is filtered off (Celite)
  3. customthe volatiles are evaporated
  4. additionDilute hydrochloric acid (50 ml) is added to the solid residue
  5. washThe resulting acidic solution is washed with ether
  6. extractionextracted twice with ether
  7. dry with materialdried (sodium sulfate)
  8. customevaporated
  9. washThe resulting crude base is eluted through an alumina column with ether-light petroleum (1:4)

Sources & evidence

ORD record
ord-d809533973b6402db5a737501a640728
Source dataset
uspto-grants-1993_05
Patent number
US05214156

Reaction notes

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