Hydrochloric Acid → 1-(N-4-Chlorobenzyl-N-methyl-amino)-3-methyl-4-isoquinoline Acetic Acid Hydrochloride

HRID 894394Notes

Reaction equation

HRID 894394 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23]([OH:25])=[O:24])=[C:14]([CH3:26])[N:13]=1.O1CCOCC1.Cl>CCOCC>[ClH:10].[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][N:2]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH2:22][C:23]([OH:25])=[O:24])=[C:14]([CH3:26])[N:13]=2)[CH3:1])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66905Benzenemethanamine, 4-chloro-N-methyl-HCID 127155131-Chloro-3-methyl-4-isoquinoline acetic acid

Product 1

HCID 705741511-(N-4-Chlorobenzyl-N-methyl-amino)-3-methyl-4-isoquinoline Acetic Acid Hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-Methyl-4-chlorobenzylamine (1.40 g., 9.0 mmol) and 1-chloro-3-methyl-4-isoquinoline acetic acid (770 mg., 3.0 mmol), prepared as in Example 8, were refluxed in 20 ml. p-dioxane for 16 hr. The cooled reaction mixture was partitioned between 200 ml ether and 50 ml 1 N sodium hydroxide. The ether rafinate was extracted with 2×30 ml 1 N sodium hydroxide. The combined basic phases were acidified to pH 6.5 with 6 N hydrochloric acid and extracted with 3×75 ml ethyl acetate. This organic phase was dried over magnesium sulfate, filtered, and vacuum evaporated to an oily residue. Chromatography of this on silica gel eluted with ethyl acetate gave an oil. The title compound was prepared from this oil by treatment with hydrochloric acid gas in ether, filtrate, and drying in vacuo; 52 mg. (4%), m/e 354.

Workup

  1. temperaturewere refluxed in 20 ml
  2. customThe cooled reaction mixture
  3. customwas partitioned between 200 ml ether and 50 ml 1 N sodium hydroxide
  4. extractionThe ether rafinate was extracted with 2×30 ml 1 N sodium hydroxide
  5. extractionextracted with 3×75 ml ethyl acetate
  6. dry with materialThis organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customvacuum evaporated to an oily residue
  9. washChromatography of this on silica gel eluted with ethyl acetate
  10. customgave an oil
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-9d59d25de06048338748b6e7eeb55b9c
Source dataset
uspto-grants-1981_08
Patent number
US04283539

Reaction notes

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