Cyclohexylamine → Ammonia

HRID 1690230Notes

Reaction equation

HRID 1690230 reaction equation
Cl[C:2]1([CH2:8][S:9]([NH:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[N:18][CH:17]=[CH:16]3)(=[O:11])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]1.[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>CO>[NH3:12].[CH:19]1[C:20]2[C:15](=[CH:14][C:13]([NH:12][S:9]([CH:8]([NH:29][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)(=[O:11])=[O:10])=[CH:22][CH:21]=2)[CH:16]=[CH:17][N:18]=1

Participants

5

Reactant 2

HCID 7965CyclohexylamineHCID 66906196HCID 66906196, compound

Product 2

HCID 222AmmoniaYield 2%HCID 57788131HCID 57788131, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To 1-chloro-N-(isoquinolin-6-yl)phenylmethanesulfonamide in MeOH is added KI and the solution is heated to 60° C. for 40 minutes. The mixture is cooled to 45° C. and cyclohexylamine is added and stirred at 45° C. After 2-4 hours or when TLC indicated completion of the reaction, 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 (SiO2, 2% NH3(2M) in MeOH/3% MeOH/CH2Cl2) gives N-(isoquinolin-6-yl)cyclohexylamino phenylmethanesulfonamide (E50).

Workup

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

Sources & evidence

ORD record
ord-66dde3cf35b348ffaa3ea9a683cee65a
Source dataset
uspto-grants-2012_04
Patent number
US08153654B2

Reaction notes

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