Morpholine → Ammonia

HRID 539567Notes

Reaction equation

HRID 539567 reaction equation
Cl[CH:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[N:11][CH:10]=[CH:9]2)=[O:4].[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>CO>[NH3:5].[CH:12]1[C:13]2[C:8](=[CH:7][C:6]([NH:5][C:3](=[O:4])[CH:2]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:15][CH:14]=2)[CH:9]=[CH:10][N:11]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 57788107HCID 57788107, compound

Product 2

HCID 222AmmoniaYield 2%HCID 57788117HCID 57788117, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To 2-chloro-2-phenyl-N-(isoquinolin-6-yl)acetamide (E39) in MeOH is added KI and the solution is heated to 60° C. for 40 minutes. The mixture is cooled to 45° C. and morpholine is added and stirred at 45° C. After 2-4 hours, the solvents are evaporated and the residue is taken up in EtOAc and extracted with NaHCO3(sat). The organics are dried (Na2SO4), filtered and evaporated. Flash chromatography (2% NH3(2M)/MeOH/3% MeOH/CH2Cl2) gives N-(isoquinolin-6-yl)-2-morpholino-2-phenyl-acetamide (E39a).

Workup

  1. temperatureThe mixture is cooled to 45° C.
  2. customthe solvents are evaporated
  3. extractionextracted with NaHCO3(sat)
  4. dry with materialThe organics are dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8bd2a566925e4e0785e5d197871bceee
Source dataset
uspto-grants-2014_10
Patent number
US08871757B2

Reaction notes

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