1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66792801, compound

HRID 534973Notes

Reaction equation

HRID 534973 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][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C)C=O>[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][CH:23]2[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]2)=[O:20])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 667508542-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid

Product 1

HCID 66792801HCID 66792801, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid (Example 44, 1.50 g, 5.12 mmol), tert-butyl 4-aminopiperidine-1-carboxylate (1.24 g, 6.2 mmol), EDCI (1.24 g, 6.2 mmol) and HOBt (0.95 g, 6.2 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature for 16 h. The reaction mixture was added to saturated NaHCO3 solution and extracted with ethyl acetate. The extract was washed with saturated NaHCO3 solution, 1M HCl and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (2.52 g, quant.) as a yellow amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated NaHCO3 solution, 1M HCl and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-304e0ef11db747f3a3ce80955e29c75b
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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