Potassium Carbonate → HCID 59410241, compound

HRID 1891354Notes

Reaction equation

HRID 1891354 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[NH2:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:12][C:8]1[C:7]2[NH:13][CH2:2][CH2:3][CH2:4][O:5][C:6]=2[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68469183HCID 68469183, compound

Product 1

HCID 59410241HCID 59410241, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To 2-(3-bromo-propoxy)-6-methyl-phenylamine (4.8 g, 20 mmol) in acetonitrile (200 mL) was added potassium carbonate (13.8 g, 100 mmol). The mixture was heated at 70° C. for 24 hrs, followed by the filtration to remove solids. After evaporation, the mixture was repartitioned with ethyl acetate (250 mL) and water (150 mL). The organic layer was then washed with brine (150 mL) and dried over MgSO4. Evaporation followed by purification by silica gel column chromatography eluting with hexane/ethyl acetate (11/1 to 4/1) yielded 1-methyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene 2-3 as a pale yellow oil (2.25 g). MS: 164.0 (M+H)+; tR=1.191 min (method 1). NMR (CDCl3), δ, 6.789-6.858 (2H, m), 6.664 (1H, t), 4.158 (2H, t), 3.343 (2H, t), 2.198 (3H, s), 1.191-2.067 (2H, m).

Workup

  1. filtrationfollowed by the filtration
  2. customto remove solids
  3. customAfter evaporation
  4. washThe organic layer was then washed with brine (150 mL)
  5. dry with materialdried over MgSO4
  6. customEvaporation
  7. customfollowed by purification by silica gel column chromatography
  8. washeluting with hexane/ethyl acetate (11/1 to 4/1)

Sources & evidence

ORD record
ord-79fa2a8d19b147fd874c9372c2c0a861
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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