Ethylamine → HCID 20283269, compound

HRID 463352Notes

Reaction equation

HRID 463352 reaction equation
[CH2:1]([NH2:3])[CH3:2].[Cl:4][CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][N:7]=1>CO.[Pd]>[ClH:4].[ClH:4].[CH2:1]([NH:3][CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][NH:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 13457433HCID 13457433, compound

Product 1

HCID 20283269HCID 20283269, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of ethylamine (100 ml) in methanol (250 ml) maintained under nitrogen and cooled in an ice bath was added portionwise 1-chloromethyl-3,4-dihydro-4-phenylisoquinoline (10.0 g, 0.033 m) and the mixture heated to 50°-52° C. for 2 hours. After cooling, the solution was poured into a pressure bottle and hydrogenated on a Parr apparatus over 10% Pd/C catalyst (2.0 g) at 40 psi for 1 hour. The catalyst was removed by filtration and the solvent evaporated to a gummy residue. This residue was dissolved in methanol (50 ml) and isopropanol (50 ml) and acidified with HCl gas. Upon cooling and standing, a white solid crystallized which was collected by filtration. Recrystallization from methanol/isopropanol/water and vacuum drying gave 7.6 g of the major isomer of 1,2,3,4-tetrahydro-1-(ethylamino)methyl-4-phenylisoquinoline dihydrochloride, m.p. 241°-242°.

Workup

  1. temperaturecooled in an ice bath
  2. temperaturethe mixture heated to 50°-52° C. for 2 hours
  3. temperatureAfter cooling
  4. customThe catalyst was removed by filtration
  5. customthe solvent evaporated to a gummy residue
  6. dissolutionThis residue was dissolved in methanol (50 ml)
  7. temperatureUpon cooling
  8. customa white solid crystallized which
  9. filtrationwas collected by filtration
  10. customRecrystallization from methanol/isopropanol/water and vacuum
  11. customdrying

Sources & evidence

ORD record
ord-8de597dfff5d40878ba4787fe21fbbd4
Source dataset
uspto-grants-1985_05
Patent number
US04518779

Reaction notes

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