Diethyl Ether → HCID 68689093, compound

HRID 1296296Notes

Reaction equation

HRID 1296296 reaction equation
Cl[CH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:13])[N:4]1[CH:14]([CH3:17])[CH2:15]Cl.C([O-])([O-])=O.[K+].[K+].[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCOCC>COCCOCCOC.CCOC(C)=O.O>[CH2:24]([N:31]1[CH2:15][CH:14]([CH3:17])[N:4]2[C:5](=[O:13])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12][CH:3]2[CH2:2]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 68693148HCID 68693148, compound

Product 1

HCID 68689093HCID 68689093, compoundYield 52.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8150DiglymeSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(chloromethyl)-2-(1-chloropropan-2-yl)-3,4-dihydroisoquinolin-1(2H)-one (from Isomer B, 0.16 g, 0.58 mmol), K2CO3 (0.16 g, 1.2 mmol), and benzylamine (0.075 ml, 0.67 mmol) in diglyme (1.5 ml) was heated at reflux for 6 h. After cooling to room temperature the reaction was transferred to a separatory funnel with ether and water. Extraction with ether and washing the organic layer with water (4×) and brine, and drying over MgSO4 afforded 0.15 g of crude product after evaporation of the solvent. Flash chromatography (SiO2, hexanes to 60% EtOAc in hexanes) afforded pure product (93 mg, 52% yield). MS (ESI) 307 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. extractionExtraction with ether
  4. washwashing the organic layer with water (4×) and brine
  5. dry with materialdrying over MgSO4
  6. customafforded 0.15 g of crude product
  7. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-b9eb28e2b7eb4a03a869cf0feac9dcb0
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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