Trifluoroacetic acid → 1-(5-(3-(Aminomethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one

HRID 2175248Notes

Reaction equation

HRID 2175248 reaction equation
[CH3:1][C:2]1[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15]([C:20]3[CH:21]=[C:22]([CH:32]=[CH:33][CH:34]=3)[CH2:23][NH:24]C(=O)OC(C)(C)C)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:24][CH2:23][C:22]1[CH:21]=[C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:14]=2[CH2:13][CH2:12][CH2:11][N:10]3[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:35]=[CH:36][CH:37]=[C:38]([CH3:39])[C:2]=2[CH3:1])[CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70982891tert-Butyl 3-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzylcarbamate

Product 1

HCID 709819111-(5-(3-(Aminomethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-oneYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzylcarbamate (0.12 g, 0.227 mmol) in DCM (2.5 mL) at 0° C. was added TFA (0.35 mL, 4.54 mmol) dropwise. The reaction mixture was slowly warmed to room temperature and stirred for 16 h. After this time, the reaction mixture was quenched with 50% saturated NaHCO3, and the aqueous phase was extracted with DCM. The combined organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford the title compound (0.075 g, 77% yield). LCMS, [M+H]+=429.2.

Workup

  1. customAfter this time, the reaction mixture was quenched with 50% saturated NaHCO3
  2. extractionthe aqueous phase was extracted with DCM
  3. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b052780a5eac4b879db50aeceeac4a9a
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

Loading…