Water → (3,4-Dichlorobenzyl)-(2-methyl-8-morpholin-4-yl-quinolin-4-yl)-amine hydrobromide

HRID 1966512Notes

Reaction equation

HRID 1966512 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[C:12]([NH2:17])[CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([CH3:18])[CH:8]=1.[Br:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28]Br.O>CN(C)C=O>[BrH:23].[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[C:12]([N:17]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([CH3:18])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21521Bis(2-bromoethyl) etherHCID 59474762N*4*-(3,4-Dichlorobenzyl)-2-methylquinoline-4,8-diamine

Product 1

HCID 68494369(3,4-Dichlorobenzyl)-(2-methyl-8-morpholin-4-yl-quinolin-4-yl)-amine hydrobromideYield 17.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N*4*-(3,4-Dichlorobenzyl)-2-methylquinoline-4,8-diamine (60.0 mg, 0.181 mmole) and bis(2-bromoethyl)ether (83.7 mg, 0.361 mmole) in dimethylformamide (1 mL), were stirred at 100° C. for 90 min in a microwave oven. Water was added and the mixture was extracted with dichloromethane. The organic phases were washed with saturated NaCl solution, dried and the solvent was removed. The residue thus obtained was purified using silica gel chromatography, eluting with dichloromethane:water 90:10. Precipitation in ethyl acetate gave a brownish solid (15 mg, 17%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic phases were washed with saturated NaCl solution
  3. customdried
  4. customthe solvent was removed
  5. customThe residue thus obtained
  6. customwas purified
  7. washeluting with dichloromethane:water 90:10
  8. customPrecipitation in ethyl acetate

Sources & evidence

ORD record
ord-76ccdd7f4bb7404387ac0ae8f053c1fe
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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