1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21186733, compound

HRID 1384286Notes

Reaction equation

HRID 1384286 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[N:15]=[C:14]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:13]3=[CH:12][C:11]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:6][CH:5]=1)(O)=[O:2].Cl.[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][NH2:33].C(N=C=NCCCN(C)C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:29][N:30]([CH2:31][CH2:32][NH:33][C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[N:15]=[C:14]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:13]3=[CH:12][C:11]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:6][CH:5]=1)=[O:2])[CH3:34]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516892Sodium BicarbonateHCID 122030063984-76-7HCID 21186704HCID 21186704, compound

Product 1

HCID 21186733HCID 21186733, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

In an atmosphere of argon, ethyl 2-(4-carboxyphenoxymethyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (1.22 g, 3.31 mmol) was dissolved in methylene chloride (5.0 ml), and the solution was mixed with N,N-dimethylethylenediamine hydrochloride (0.44 ml, 4.01 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) hydrochloride (954.2 mg, 4.98 mmol) at 0° C. and then stirred at room temperature for 15 hours. The reaction solution was diluted with chloroform, mixed with saturated sodium bicarbonate aqueous solution and then extracted with chloroform. The thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1) to obtain the title compound (767.2 mg, 52.7%) as pale yellow amorphous.

Workup

  1. extractionextracted with chloroform
  2. washThe thus obtained organic layer was washed with water and saturated brine in that order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-19f9c4bdf9114e54b292b3b5c48fb699
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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