1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-benzyl-2-(4-(2-tert-butylphenyl)-piperazin-1-yl)-N-isopropyl-2-oxoacetamide

HRID 534909Notes

Reaction equation

HRID 534909 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](O)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:43]([NH:50][CH:51]([CH3:53])[CH3:52])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C(Cl)Cl>[CH2:43]([N:50]([CH:51]([CH3:53])[CH3:52])[C:18](=[O:19])[C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:12][CH2:13]1)=[O:21])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66024IsopropylbenzylamineHCID 757711-HydroxybenzotriazoleHCID 667508542-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid

Product 1

HCID 66751325N-benzyl-2-(4-(2-tert-butylphenyl)-piperazin-1-yl)-N-isopropyl-2-oxoacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-(2-tert-butylphenyl)piperazin-1-yl)-2-oxo-acetic acid (0.091 g, 0.31 mmol) in methylene chloride (5.0 mL) was added EDCI (0.078 g, 0.41 mmol) and HOBt (0.055 g, 0.41 mmol) at room temperature. After 40 min N-benzylpropan-2-amine (0.054 g, 0.36 mmol) was added at room temperature. After 16 h the reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography (silica gel, 80:20 to 70:30 heptane/ethyl acetate, gradient elution) to provide N-benzyl-2-(4-(2-tert-butylphenyl)-piperazin-1-yl)-N-isopropyl-2-oxoacetamide as a mixture of cis and trans isomers (0.041 g, 32%) as a white solid, mp 65-68° C.

Workup

  1. concentrationAfter 16 h the reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash column chromatography (silica gel, 80:20 to 70:30 heptane/ethyl acetate, gradient elution)

Sources & evidence

ORD record
ord-bd7f1ef92e1c485d86fd1d394682db33
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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