Sodium Hydroxide → HCID 22272840, compound

HRID 1064824Notes

Reaction equation

HRID 1064824 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([NH:13][C:14]2[C:19]([CH:20]([CH3:22])[CH3:21])=[CH:18][C:17]([OH:23])=[CH:16][C:15]=2[CH:24]([CH3:26])[CH3:25])=[O:12])[CH2:6][CH2:5]1.[CH:27](N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C.[OH-].[Na+]>C(#N)C.CO>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([NH:13][C:14]2[C:19]([CH:20]([CH3:21])[CH3:22])=[CH:18][C:17]([O:23][CH3:27])=[CH:16][C:15]=2[CH:24]([CH3:26])[CH3:25])=[O:12])[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 22272790HCID 22272790, compound

Product 1

HCID 22272840HCID 22272840, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Into a solution of the acetamide (640 mg, 1.76 mmol) in a mixed solvent (10 ml) of methanol and acetonitrile (1:4) were dropped N,N-diisopropylethylamine (0.43 ml, 2.46 mmol) and trimethylsilyl diazomethane (1.23 ml, 2.46 mmol) and the mixture was stirred for 12 hours. The residue obtained by evaporation of the solvent was made alkaline by adding 2N sodium hydroxide and then extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate and the solvent was evaporated therefrom to provide 550 mg (yield 83%) of 2-[4-(2-hydroxyethyl)piperazin-1-yl]-N-(2,6-diisopropyl-4-methoxyphenyl)acetamide as colorless crystals.

Workup

  1. customThe residue obtained by evaporation of the solvent
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution successively and dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7bbc9b47ba84479ca648f28d89bc0b94
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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