Hydrochloric Acid → HCID 69412740, compound

HRID 1272348Notes

Reaction equation

HRID 1272348 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1([CH3:31])[CH:12]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:11]2[C:18]([CH3:30])=[C:19]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[C:20]([CH3:23])=[C:21]([CH3:22])[C:10]=2[O:9]1.CS(O[CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH3:46])[CH:40]=1)(=O)=O.[ClH:47]>C(#N)C.C(OCC)(=O)C>[ClH:47].[ClH:47].[CH3:46][O:45][C:41]1[CH:40]=[C:39]([CH2:38][CH2:37][N:27]2[CH2:26][CH2:25][N:24]([C:19]3[C:20]([CH3:23])=[C:21]([CH3:22])[C:10]4[O:9][C:8]([CH3:31])([CH3:7])[CH:12]([N:13]5[CH2:14][CH2:15][CH2:16][CH2:17]5)[C:11]=4[C:18]=3[CH3:30])[CH2:29][CH2:28]2)[CH:44]=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 9902690HCID 9902690, compoundHCID 130615423-Methoxyphenethyl mesylate

Product 1

HCID 69412740HCID 69412740, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of potassium carbonate (207 mg, 1.1 mmol) and (2,2,4,6,7-pentamethyl-3-pyrrolidinyl-2,3-dihydro-1-benzofuran-5-yl)piperazine obtained in Example 134 in acetonitrile (5 ml) was added 3-methoxyphenethyl methanesulfonate (253 mg) at room temperature. After the mixture was stirred for 16 hours, the resulting mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The organic extract was washed saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified with basic silica gel column chromatography (ethyl acetate/hexane=4/1) to obtain 186 mg as a free base. The free base was treated with 4N hydrogenchloride in ethyl acetate (10 mL) to obtain 137 mg (yield 25%) of the title compound. mp. 183–185° C. (decomposition) (ethanol-ethyl acetate).

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified with basic silica gel column chromatography (ethyl acetate/hexane=4/1)
  9. customto obtain 186 mg as a free base

Sources & evidence

ORD record
ord-1de0d51b42cc4f72aa37b68dc0156b2d
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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