Dimethylamine → HCID 20283262, compound

HRID 463350Notes

Reaction equation

HRID 463350 reaction equation
[CH3:1][NH:2][CH3:3].[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>CO.[Pd]>[ClH:4].[ClH:4].[CH3:1][N:2]([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)[CH3:3]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 13457433HCID 13457433, compound

Product 1

HCID 20283262HCID 20283262, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of dimethylamine (250 ml) in methanol (1 liter) maintained under nitrogen and cooled in an ice bath was added portionwise 1-chloromethyl-3,4-dihydro-4-phenylisoquinoline (25.0 g, 0.084 m) and the mixture stirred for 4 hours while being allowed to warm to ambient temperature. 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. The residue was dissolved in methanol (300 ml) and isopropanol (100 ml) and acidified with HCl gas. Upon cooling and standing, a solid crystallized which was collected by filtration. Recrystallization from methanol/isopropanol/water gave 12.2 g of the major isomer of 1,2,3,4-tetrahydro-1-dimethylaminomethyl-4-phenylisoquinoline dihydrochloride as a monohydrate, m.p. 278°-279°.

Workup

  1. temperaturecooled in an ice bath
  2. waitfor 16 hours
  3. customThe catalyst was removed by filtration
  4. customthe solvent evaporated to a gummy residue
  5. dissolutionThe residue was dissolved in methanol (300 ml)
  6. temperatureUpon cooling
  7. customa solid crystallized which
  8. filtrationwas collected by filtration
  9. customRecrystallization from methanol/isopropanol/water

Sources & evidence

ORD record
ord-ee30b1ce328a4c79b8ba32cf32a27f3a
Source dataset
uspto-grants-1985_05
Patent number
US04518779

Reaction notes

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