2-Methoxybenzylamine → 1-[(2-Methoxyphenylmethyl)amino]-6,7-dimethoxyisoquinoline hydrochloride

HRID 1589831Notes

Reaction equation

HRID 1589831 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([Cl:15])=[N:8][CH:7]=[CH:6]2.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][NH2:21]>C(Cl)(Cl)Cl>[ClH:15].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][NH:21][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 812922-MethoxybenzylamineHCID 106407081-Chloro-6,7-dimethoxyisoquinoline

Product 1

HCID 197710081-[(2-Methoxyphenylmethyl)amino]-6,7-dimethoxyisoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6,7-Dimethoxy-1-chloroisoquinoline (J. Am. Pharm. Assoc., Sci. Ed. (1952), 41, 643-50; C.A. 47, 11205d.) (1.0 gm, 0.00447 mol) and 2-methoxybenzylamine (1.22 gm, 0.00894 mol) were mixed at room temperature and heated, with stirring, in an oil-bath at 140° for 1.5 hours. After cooling the mixture was dissolved in chloroform and the solution washed with saturated NaHCO3 solution and water, dried and evaporated. The resulting oil was chromatographed on silica gel, using chloroform as eluent. Fractions were monitored by t.l.c. and those containing pure product were combined, evaporated to dryness and the residue (0.25 g) dissolved in ethanol containing ethanolic hydrogen chloride. This solution was evaporated to dryness and the residue crystallised from ethanol/diethyl ether to give the title compound as its hydrochloride salt (0.22 gm), m.p. 225°-229°.

Workup

  1. temperatureheated
  2. temperatureAfter cooling the mixture
  3. washthe solution washed with saturated NaHCO3 solution and water
  4. customdried
  5. customevaporated
  6. customThe resulting oil was chromatographed on silica gel
  7. customevaporated to dryness
  8. dissolutionthe residue (0.25 g) dissolved in ethanol containing ethanolic hydrogen chloride
  9. customThis solution was evaporated to dryness
  10. customthe residue crystallised from ethanol/diethyl ether

Sources & evidence

ORD record
ord-74d5f331257f4378b607efa606b054bd
Source dataset
uspto-grants-1993_04
Patent number
US05200417

Reaction notes

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