Water → (1-(2-Methoxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl)methanol

HRID 928420Notes

Reaction equation

HRID 928420 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][OH:12])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Br[CH2:14][CH2:15][O:16][CH3:17].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH3:17][O:16][CH2:15][CH2:14][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][OH:12])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl ether3×HCID 66723433(1,2,3,4-Tetrahydroquinolin-7-yl)methanol

Product 1

HCID 58081319(1-(2-Methoxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (1,2,3,4-tetrahydroquinolin-7-yl)methanol (370 mg, 1.496 mmol), 1-bromo-2-methoxyethane (0.141 ml, 1.496 mmol) and Cs2CO3 (731 mg, 2.244 mmol) in DMF (10 ml). was stirred for 16 hr at 80° C. Additional 1-bromo-2-methoxyethane (0.070 ml, 0.748 mmol) was added and stirring was continued for 16 hr at 80° C. A third batch of 1-bromo-2-methoxyethane (0.070 ml, 0.748 mmol) was added and stirring was continued for 1 additional hour at 80° C. The reaction mixture was cooled to room temperature and water was added. The mixture was extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give the title compound. HPLC (Method A) Rt=1.173 min; MS (Method A) [M+H]+=221.9

Workup

  1. stirringstirring
  2. waitwas continued for 16 hr at 80° C
  3. stirringstirring
  4. customwas continued for 1 additional hour at 80° C
  5. temperatureThe reaction mixture was cooled to room temperature
  6. extractionThe mixture was extracted with AcOEt
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c948d02c59b469caebe7c0e11dcafe3
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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