Dimethylformamide → 1-Phenoxy-3-[2-(2-methylquinolin-4-ylamino)-ethylamino]-propan-2-ol

HRID 1903798Notes

Reaction equation

HRID 1903798 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][C:13]1[CH:22]=[C:21]([NH:23][CH2:24][CH2:25][NH2:26])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.CN(C)C=O>C(Cl)Cl>[O:5]([CH2:1][CH:2]([OH:4])[CH2:3][NH:26][CH2:25][CH2:24][NH:23][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]([CH3:12])[CH:22]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31217Phenyl glycidyl etherHCID 6471895N1-(2-Methylquinolin-4-yl)ethane-1,2-diamine

Product 1

HCID 204667251-Phenoxy-3-[2-(2-methylquinolin-4-ylamino)-ethylamino]-propan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.4 g. phenyl glycidyl ether and 12 g. 2-methyl-4-(2-aminoethylamino)-quinoline in 60 ml. dimethylformamide is left to stand for 48 hours at ambient temperature. The reaction mixture is then taken up in methylene chloride, washed with water, dried and purified chromatographically on a silica gel column using, as elution agent, methylene chloride-methanoltriethylamine (26:3:0.6 v/v/v), and then recrystallized from isopropyl alcohol. There are obtained 3.5 g. (34% of theory) of the desired product in the form of colorless crystals; m.p. 151°-152° C.

Workup

  1. washwashed with water
  2. customdried
  3. custompurified chromatographically on a silica gel column
  4. washusing, as elution agent, methylene chloride-methanoltriethylamine (26:3:0.6 v/v/v)
  5. customrecrystallized from isopropyl alcohol
  6. customThere are obtained 3.5 g

Sources & evidence

ORD record
ord-704104ca0fba42b883c589c1d1cb68cf
Source dataset
uspto-grants-1984_03
Patent number
US04438128

Reaction notes

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