Hexane → HCID 69730844, compound

HRID 1064841Notes

Reaction equation

HRID 1064841 reaction equation
[CH:1](N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C.CCCCCC.[CH:23]([C:26]1[C:31]([OH:32])=[CH:30][CH:29]=[C:28]([CH:33]([CH3:35])[CH3:34])[C:27]=1[NH:36][C:37](=[O:49])[CH2:38][N:39]1[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][CH2:47][OH:48])[CH2:41][CH2:40]1)([CH3:25])[CH3:24]>C(#N)C.CO>[CH:23]([C:26]1[C:31]([O:32][CH3:1])=[CH:30][CH:29]=[C:28]([CH:33]([CH3:35])[CH3:34])[C:27]=1[NH:36][C:37](=[O:49])[CH2:38][N:39]1[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][CH2:47][OH:48])[CH2:41][CH2:40]1)([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 69731075HCID 69731075, compound

Product 1

HCID 69730844HCID 69730844, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

N,N-Diisopropylethylamine (513 mg, 3.97 mmol) and a solution of trimethylsilyl diazomethane in hexane (2.0 M, 2.0 ml, 3.97 mmol) were added to a solution of N-(2,6-diisopropyl-3-hydroxyphenyl)-2-[4-(3-hydroxypropyl) piperazin-1-yl]acetamide (500 mg, 1.32 mmol) in a mixed solvent of methanol (8 ml) and acetonitrile (12 ml) and the mixture was stirred for four days. After the reaction, the solvent was evaporated. The residue was made basic by adding an aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (developing solvent, chloroform methanol=10:1) to provide 449 mg (yield 87%) of N-(2,6-diisopropyl-3-methoxyphenyl)-2-[4-(3-hydroxypropyl) piperazin-1-yl]acetamide.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated
  3. additionby adding an aqueous solution of sodium bicarbonate
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by a silica gel column chromatography (developing solvent, chloroform methanol=10:1)

Sources & evidence

ORD record
ord-b1bfe4f8c6f4478e909d5c96150bc195
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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