Aluminum(III) Chloride → 3-(2-Amino-6-phenoxy-3,4-dihydro-quinolin-3-yl)-N-cyclohexyl-N-methyl-propionamide

HRID 252465Notes

Reaction equation

HRID 252465 reaction equation
[CH:1]1([N:7]([CH3:30])[C:8](=[O:29])[CH2:9][CH2:10][CH:11]([C:27]#[N:28])[CH2:12][C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=[CH:15][C:14]=2[NH2:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[NH2:28][C:27]1[CH:11]([CH2:10][CH2:9][C:8]([N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH3:30])=[O:29])[CH2:12][C:13]2[C:14](=[CH:15][CH:16]=[C:17]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:18]=2)[N:26]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 672689265-(2-Amino-5-phenoxy-phenyl)-4-cyano-pentanoic acid cyclohexyl-methyl-amide

Product 1

HCID 594281643-(2-Amino-6-phenoxy-3,4-dihydro-quinolin-3-yl)-N-cyclohexyl-N-methyl-propionamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(2-amino-5-phenoxy-phenyl)-4-cyano-pentanoic acid cyclohexyl-methyl-amide (0.20 g, 0.46 mmol) was dissolved in toluene (5 mL), followed by addition of aluminum chloride (0.184 g, 1.38 mmol). The reaction mixture was heated to reflux for 10 minutes and was then allowed to cool to room temperature. The crude reaction mixture was poured into a separatory funnel and partitioned between ethyl acetate and 10% aqueous Na2CO3 solution. The organic layer was washed 2 more times with 10% aqueous Na2CO3 solution and one time with saturated brine solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield a residue which was purified by flash chromatography using chloroform:methanol:triethylamine as the mobile phase to yield the title compound as a residue.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 10 minutes
  3. customThe crude reaction mixture
  4. additionwas poured into a separatory funnel
  5. custompartitioned between ethyl acetate and 10% aqueous Na2CO3 solution
  6. washThe organic layer was washed 2 more times with 10% aqueous Na2CO3 solution and one time with saturated brine solution
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customto yield a residue which
  10. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-45b94f456c4d4e74834083ba46a1a30e
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

Loading…