Methylamine → HCID 70409025, compound

HRID 462723Notes

Reaction equation

HRID 462723 reaction equation
[CH3:1][NH2:2].[ClH:3].[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>[Pd].CO>[ClH:4].[ClH:3].[CH3:1][NH:2][CH2:5][C@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@@H:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][NH:7]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 134574341-(Chloromethyl)-4-phenyl-3,4-dihydroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 70409025HCID 70409025, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of methanol (1 liter) and monomethylamine (300 ml) maintained under nitrogen and cooled in an ice bath was added portionwise 1-chloromethyl-3,4-dihydro-4-phenylisoquinoline hydrochloride (83.0 g, 0.28 m) and the mixture heated to reflux (ca 50°-55°) for 2 hours. After cooling, the solution was poured into a pressure bottle and hydrogenated on a Parr apparatus over 5% Pd/C catalyst (5.0 g) at 40 psi for 16 hours. The catalyst was removed by filtration and the solvent evaporated to a gummy residue. This was dissolved in a mixture of methanol (200 ml) and isopropanol (200 ml) and acidified with HCl gas. Upon cooling and standing, a white solid crystallized which was collected by filtration and dried to give 64.0 g of the major isomer cis-1,2,3,4-tetrahydro-1-methylaminomethyl-4-phenyl-isoquinoline dihydrochloride, m.p. 276°-277°. A second crop of solid was obtained from the crystallization (26.1 g) which consisted (TLC) mostly of the minor isomer. Two recrystallizations of this crop provide the pure minor isomer trans-1,2,3,4-tetrahydro-1-methylaminomethyl-4-phenylisoquinoline, m.p. 269°-270°.

Workup

  1. temperaturecooled in an ice bath
  2. temperaturethe mixture heated
  3. temperatureto reflux (ca 50°-55°) for 2 hours
  4. temperatureAfter cooling
  5. customThe catalyst was removed by filtration
  6. customthe solvent evaporated to a gummy residue
  7. dissolutionThis was dissolved in a mixture of methanol (200 ml) and isopropanol (200 ml)
  8. temperatureUpon cooling
  9. customa white solid crystallized which
  10. filtrationwas collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-72de29d285dc43f18b383c3eb1c1829b
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

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