1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-N-(2-hydroxy-2-methylpropyl)-2-oxoacetamide

HRID 534937Notes

Reaction equation

HRID 534937 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][CH2:23][C:24]([CH3:27])([OH:26])[CH3:25].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][CH2:23][C:24]([OH:26])([CH3:27])[CH3:25])=[O:20])[CH2:15][CH2:16]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 951022-Propanol, 1-amino-2-methyl-HCID 516892Sodium BicarbonateHCID 667508542-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid

Product 1

HCID 667513542-[4-(2-tert-butylphenyl)piperazin-1-yl]-N-(2-hydroxy-2-methylpropyl)-2-oxoacetamideYield 102.1%

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), 1-amino-2-methylpropan-2-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 provide 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-N-(2-hydroxy-2-methylpropyl)-2-oxoacetamide (0.380 g, quant) 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

Sources & evidence

ORD record
ord-663376e80fba43bbac9de3ee4e8c9a3b
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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