Methylamine → HCID 20283264, compound

HRID 463349Notes

Reaction equation

HRID 463349 reaction equation
[CH3:1][NH2:2].[Cl:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][N:6]=1>CO>[ClH:3].[CH3:1][NH:2][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13457443HCID 13457443, compound

Product 1

HCID 20283264HCID 20283264, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of monomethylamine (200 ml) and methanol (1 liter) maintained under nitrogen and cooled in an ice bath was added a solution of 1-chloromethyl-4-phenylisoquinoline (24.3 g, 0.093 m) in methanol (100 ml) and the mixture allowed to warm to ambient temperature and stirred for 3 days. The solvents were evaporated and the dark oily residue dissolved in methanol (50 ml) and isopropanol and acidified with HCl gas. Upon cooling and standing, a white solid crystallized which was collected by filtration and dried to give 16.3 g 1-methylaminomethyl-4-phenylisoquinoline hydrochloride, m.p. 212°-213°. An analytical sample, recrystallized from methanol/ethanol, had m.p. 215°-216°.

Workup

  1. temperaturecooled in an ice bath
  2. customThe solvents were evaporated
  3. dissolutionthe dark oily residue dissolved in methanol (50 ml)
  4. temperatureUpon cooling
  5. customa white solid crystallized which
  6. filtrationwas collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-7d036a3b791943f49efb01fac398e523
Source dataset
uspto-grants-1985_05
Patent number
US04518779

Reaction notes

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