Dipropylamine → HCID 22559930, compound

HRID 1854690Notes

Reaction equation

HRID 1854690 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)=[O:2].C(N(CC)C(C)C)(C)C.[CH2:21]([NH:24][CH2:25][CH2:26][CH3:27])[CH2:22][CH3:23]>ClCCl.C(OCC)C>[CH2:21]([N:24]([CH2:25][CH2:26][CH3:27])[C:6]([C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=1)[CH:1]=[O:2])=[O:8])[CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 8902DipropylamineHCID 120773-CarboxybenzaldehydeHCID 81531Diisopropylethylamine

Product 1

HCID 22559930HCID 22559930, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-formylbenzoic acid (300 mg, 2.00 mmol), N,N-diisopropylethylamine (0.70 mL, 4.0 mmol), and di-n-propylamine (0.41 mL, 3.0 mmol) in 4 mL of dry dichloromethane was added 1-ethyl-3-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride (575 mg, 3.00 mmol) at 0° C. After being stirred at room temperature overnight, the reaction mixture was diluted with diethyl ether. The solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo to obtain the title compound as a colorless oil (95 mg, 20%).

Workup

  1. washThe solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b4f035a53c1345b3a0e2d0866b863fec
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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