Water → HCID 86683406, compound

HRID 579431Notes

Reaction equation

HRID 579431 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[CH:14]=[O:15])[CH2:10][NH:9][CH2:8][CH2:7]2.C([O-])([O-])=O.[K+].[K+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C)C=O>[CH2:22]([N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:13]([CH:14]=[O:15])=[C:4]([O:3][CH3:2])[CH:5]=2)[CH2:10]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 86683407HCID 86683407, compound

Product 1

HCID 86683406HCID 86683406, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-methoxy-1,2,3,4-tetrahydro-isoquinoline-7-carbaldehyde hydrochloride (114 mg, 0.5 mmol) and freshly dried K2CO3 (173 mg, 1.25 mmol) in anhydrous dimethylformamide (5 mL), benzyl chloride (69 μL, 76 mg, 0.6 mmol) was added and the mixture was stirred at room temperature for 24 h. The mixture was poured into water (25 mL) and extracted with diethyl ether (3×10 mL). The combined organic layers were washed with brine (3×5 mL), dried over MgSO4 and concentrated. The title compound (112 mg, 0.40 mmol, 80%) was obtained as a yellow oil.

Workup

  1. additionwas added
  2. extractionextracted with diethyl ether (3×10 mL)
  3. washThe combined organic layers were washed with brine (3×5 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3402e24655cb4715b3a7cc60bc5279d9
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

Loading…