Water → HCID 20237819, compound

HRID 365200Notes

Reaction equation

HRID 365200 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.[CH3:12][O:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([NH:24][CH2:25][CH2:26][NH2:27])=[N:16][CH:15]=1.O>CN(C)C=O>[O:5]([CH2:1][CH:2]([OH:4])[CH2:3][NH:27][CH2:26][CH2:25][NH:24][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([O:13][CH3:12])=[CH:15][N:16]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31217Phenyl glycidyl etherHCID 20237891N1-(4-Methoxy-1-isoquinolinyl)-1,2-ethanediamine

Product 1

HCID 20237819HCID 20237819, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.2 g. Phenyl glycidyl ether and 15 g. 4-methoxy-1-(2-aminoethylamino)-isoquinoline are dissolved in dimethylformamide and left to stand for 72 hours at ambient temperature. The reaction mixture is then poured into water, extracted with methylene chloride, dried and purified chromatographically on a silica gel column using, as elution agent, methylene chloride-methanol-triethylamine (8:1:0.05 v/v/v). By evaporation of the pure fractions, there are obtained 5.5 g. (44% of theory) of an oil. By the addition of 1.7 g. fumaric acid to a solution of this oil in ethyl acetate-ethanol, a hydrogen fumarate is precipitated out and this is then recrystallized from isopropyl alcohol. The desired product is obtained in the form of colorless crystals; m.p. 152°-153° C.

Workup

  1. waitleft
  2. extractionextracted with methylene chloride
  3. customdried
  4. custompurified chromatographically on a silica gel column
  5. washusing, as elution agent, methylene chloride-methanol-triethylamine (8:1:0.05 v/v/v)
  6. customBy evaporation of the pure fractions, there
  7. customare obtained 5.5 g
  8. additionBy the addition of 1.7 g
  9. customfumaric acid to a solution of this oil in ethyl acetate-ethanol, a hydrogen fumarate is precipitated out
  10. customthis is then recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-3c6dcca7bea5418197b47c36421bae60
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

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