Triethylamine → HCID 178471809, compound

HRID 1961623Notes

Reaction equation

HRID 1961623 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:14])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][CH2:8]1)[CH3:3].Cl.[N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26]([Cl:28])=[O:27])=[CH:18][CH:17]=1.C(N(CC)CC)C.CCCCCCC.CCOC(C)=O>ClCCl.CCOC(C)=O>[ClH:28].[CH2:2]([O:4][C:5](=[O:14])[CH2:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([NH:13][C:26]([C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:16]=[CH:17][CH:18]=2)=[O:27])[CH2:11][CH2:12]1)[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12373997Quinoline-4-carbonyl chloride hydrochlorideHCID 21899848Ethylacetate heptaneHCID 178471807HCID 178471807, compound

Product 1

HCID 178471809HCID 178471809, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Trans-(4-Amino-cyclohexyl)-acetic acid ethyl ester hydrochloride (3.63 g, 17 mmol) is solved in dichloromethane (115 mL) and quinoline-4-carbonyl chloride hydrochloride is added (4.184 g, 18 mmol) followed by the slow addition of triethylamine (11.3 mL, 81 mmol) at 0° C. The mixture is stirred at room temperature overnight and the salts obtained are removed by filtration and the filtrate is extracted. The organic layer is washed with NaHCO3 and brine. The organic phases are dried and concentrated to obtain 3.8 g of a crude. After a flash chromatography with heptane/AcOEt 4:1 to AcOEt a solid was obtained that was recrystallized with EtOAc and n-heptane to obtain the title compound as a pink solid (2.72 g, 42% yield). MS (m/e): 341.3 (M+H+).

Workup

  1. customthe salts obtained
  2. customare removed by filtration
  3. extractionthe filtrate is extracted
  4. washThe organic layer is washed with NaHCO3 and brine
  5. customThe organic phases are dried
  6. concentrationconcentrated
  7. customto obtain 3.8 g of a crude
  8. customthat was recrystallized with EtOAc and n-heptane

Sources & evidence

ORD record
ord-5198bdffeefc4d6abc54345b79c623f9
Source dataset
uspto-grants-2013_04
Patent number
US08415350B2

Reaction notes

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