Triethylamine → HCID 178501158, compound

HRID 2109059Notes

Reaction equation

HRID 2109059 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1)=[O:4].Cl.[CH3:15][NH:16][CH3:17].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:15][N:16]([CH3:17])[C:11]([C@H:8]1[CH2:9][CH2:10][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7]1)=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178501163HCID 178501163, compound

Product 1

HCID 178501158HCID 178501158, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (20.0 g) obtained in Reference Example 1(2) is dissolved in chloroform (200 ml), and thereto are added dimethylamine hydrochloride (10.5 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (24.7 g) and triethylamine (26.0 g) under ice-cooling. The mixture is then stirred at room temperature for 17 hours. Ice-water is poured to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively and dried over sodium sulfate. The solvent is concentrated under reduced pressure and the resulting residue is purified by silica gel column chromatography (eluent: chloroform, followed by chloroform/methanol=20/1) to give methyl trans-4-[(dimethylamino)carbonyl]-cyclohexanecarboxylate (20.1 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively
  4. dry with materialdried over sodium sulfate
  5. concentrationThe solvent is concentrated under reduced pressure
  6. customthe resulting residue is purified by silica gel column chromatography (eluent: chloroform, followed by chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-1929c5033357451db87ecd6a103ddd2f
Source dataset
uspto-grants-2009_04
Patent number
US07514449B2

Reaction notes

Loading…