Hydrochloric Acid → 9b-Allyl-3-cyclopropylmethyl-8-methoxy-5,9b-dihydrobenz[e]indoline

HRID 26399Notes

Reaction equation

HRID 26399 reaction equation
[CH2:1]([C:4]1([CH2:20][CH2:21][NH:22][CH2:23][CH:24]2[CH2:26][CH2:25]2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][C:5]21OCCO2)[CH:2]=[CH2:3].Cl>C(O)C>[CH2:1]([C:4]12[C:13]3[CH:12]=[C:11]([O:14][CH3:15])[CH:10]=[CH:9][C:8]=3[CH2:7][CH:6]=[C:5]1[N:22]([CH2:23][CH:24]1[CH2:26][CH2:25]1)[CH2:21][CH2:20]2)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23330777HCID 23330777, compound

Product 1

HCID 233307859b-Allyl-3-cyclopropylmethyl-8-methoxy-5,9b-dihydrobenz[e]indoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation From 1-allyl-1-[2-(N-cyclopropylmethylamino)ethyl]-2,2-ethylenedioxy-7-methoxy-1,2,3,4-tetrahydronaphthalene (XIXa). To a solution of 30.4 g (85 mmole) XIXa in ethanol (125 ml) was added a solution of 4% hydrochloric acid (125 ml). The reaction mixture was stirred at room temperature overnight (16 hrs) and then concentrated under vacuum to about half volume, alkalified with 10% sodium hydroxide and extracted with ether (2×100 ml). Combined extracts were washed with water (2×80 ml) and dried (MgSO4). Removal of the solvent under vacuum gave 23.0 g (92%) IIe identical with the material prepared in Example 39(a) above.

Workup

  1. concentrationconcentrated under vacuum to about half volume
  2. extractionextracted with ether (2×100 ml)
  3. washCombined extracts were washed with water (2×80 ml)
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent under vacuum

Sources & evidence

ORD record
ord-f9f74f28753243f0abb43d0274eb32c1
Source dataset
uspto-grants-1979_04
Patent number
US04150032

Reaction notes

Loading…