Dimethylformamide → HCID 9948591, compound

HRID 1682578Notes

Reaction equation

HRID 1682578 reaction equation
[CH2:1]([N:4]([CH2:23][CH2:24][CH3:25])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8](OS(C(F)(F)F)(=O)=O)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[CH3:26][Sn](C)(C)C.[Cl-:31].[Li+].CN(C)[CH:35]=[O:36]>>[ClH:31].[C:35]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[CH2:6][CH:5]([N:4]([CH2:23][CH2:24][CH3:25])[CH2:1][CH2:2][CH3:3])[CH2:14][CH2:13]2)(=[O:36])[CH3:26]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11661TetramethyltinHCID 433294Lithium ChlorideHCID 14973078HCID 14973078, compound

Product 1

HCID 9948591HCID 9948591, compoundYield 70%

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(dipropylamino)-8-[(trifluoromethylsulfonyl)-oxy]tetralin (455 mg, 1.2 mmol), tetramethylstannane (257 mg, 1.44 mmol), lithium chloride (158 mg, 3.7 mmol), dichloro[1,1'-bis(diphenylphosphino)ferocene]palladium(II) (PdCl2 (dppf); 61 mg, 0.07 mmol), molecular sieves (4 Å; 120 mg) and dimethylformamide (10 ml) was stirred under an atmosphere of carbon monoxide for 14 h at 90° C. The catalyst was filtered and the filtrate was partitioned between water and ether. The organic layer was dried (sodium sulfate) and concentrated in vacuo. The residue was purified by chromatography on an alumina column eluted with ether/light petroleum 1:16. Pure fractions were pooled and concentrated and the resulting oil was treated with ethereal hydrogen chloride to afford 158 mg (70%) of pure 8-acetyl-2-(dipropylamino)tetralin hydrochloride, which could be recrystallised from CHCl3 and diethylether. Mp 125°-127° C.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate was partitioned between water and ether
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on an alumina column
  6. washeluted with ether/light petroleum 1:16
  7. concentrationconcentrated
  8. additionthe resulting oil was treated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-df2ca07203134e6eaced93dd122193ed
Source dataset
uspto-grants-1997_06
Patent number
US05635537

Reaction notes

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