Morpholine → HCID 69199563, compound

HRID 900706Notes

Reaction equation

HRID 900706 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10](=[O:27])[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[C:15](Cl)=[N:14][CH:13]=1)[CH3:8]>C1(C)C=CC=CC=1>[CH2:7]([O:9][C:10](=[O:27])[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[C:15]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[N:14][CH:13]=1)[CH3:8]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86588461HCID 86588461, compound

Product 1

HCID 69199563HCID 69199563, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Excess morpholine is added to a suspension of (1-chloro-6,7-dimethoxy-isoquinolin-4-yl)-acetic acid ethyl ester (0.200 g, 0.65 mmol) in toluene (1 ml) and the mixture heated to reflux until the starting material is consumed. After evaporation, the residue is partitioned between water and dichloromethane, the organic phase is dried over magnesium sulfate and evaporated to afford (6,7-dimethoxy-1-morpholin-4-yl-isoquinolin-4-yl)-acetic acid ethyl ester [MH]+ 361. The crude ester (0.240 g, 0.66 mmol) is dissolved in ethanol (20 ml), treated with 2M sodium hydroxide (3 ml) and stirred at room temperature overnight. After adjustment to pH 1 with concentrated hydrochloric acid, the solvent is evaporated and the crude acid used directly for formation of the xanthine derivative.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux until the starting material
  3. customis consumed
  4. customAfter evaporation
  5. customthe residue is partitioned between water and dichloromethane
  6. dry with materialthe organic phase is dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-7f1a51037a194d86b7fc87d1318fbed3
Source dataset
uspto-grants-2008_04
Patent number
US07361661B2

Reaction notes

Loading…