2-Amino-2-methyl-1-propanol → 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-N-(2-hydroxy-1,1-dimethylethyl)-2-oxoacetamide

HRID 534938Notes

Reaction equation

HRID 534938 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:21])[C:18]([OH:20])=O)[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[NH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][OH:25].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(=O)([O-])O.[Na+]>C(#N)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:21])[C:18]([NH:22][C:23]([CH3:27])([CH3:26])[CH2:24][OH:25])=[O:20])[CH2:15][CH2:16]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 118072-Amino-2-methyl-1-propanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 667508542-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid

Product 1

HCID 667927252-[4-(2-tert-butylphenyl)piperazin-1-yl]-N-(2-hydroxy-1,1-dimethylethyl)-2-oxoacetamideYield 81.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of [4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetic acid (Example 44, 0.300 g, 1.03 mmol), 2-amino-2-methylpropan-1-ol (0.111 g, 1.24 mmol), EDCI (0.238 g, 1.24 mmol) and HOBt (0.168 g, 1.24 mmol) in acetonitrile (5 mL) was stirred at room temperature for 16 h. The reaction mixture was poured into saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate solution and brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to give the crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=80:20 to 40:60) to provide 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-N-(2-hydroxy-1,1-dimethylethyl)-2-oxoacetamide (0.302 g, 81%) as a white amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium hydrogen carbonate solution and brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. customto give the crude product
  6. customThe product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=80:20 to 40:60)

Sources & evidence

ORD record
ord-28f8710736364a1abd65110dec719a30
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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