Water → HCID 66625363, compound

HRID 1629678Notes

Reaction equation

HRID 1629678 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:12]=2)[C@@H:7]([O:19][C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)[CH2:6][C@@H:5]1[CH3:27])(=[O:3])[CH3:2].C(N(CC)C(C)C)(C)C.Br[CH2:38][CH2:39][O:40][CH2:41][CH2:42]Br.O>C1(C)C=CC=CC=1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:12]=2)[C@@H:7]([O:19][C:20]2[CH:21]=[CH:22][C:23]([N:26]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:24][CH:25]=2)[CH2:6][C@@H:5]1[CH3:27])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 66625187HCID 66625187, compound

Product 1

HCID 66625363HCID 66625363, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(Step 6) 66.1 mg of ethyl (2S,4S)-1-acetyl-4-(4-aminophenoxy)-2-methyl-1,2,3,4-tetrahydroquinoline-6-carboxylate was dissolved in 2 mL of toluene, and 312 μL of N,N-diisopropylethylamine and 113 μL of 2-bromoethyl ether were added to the solution at 0° C. The mixture was heated to reflux for 14 hours. After completion of the reaction, the reaction liquid was cooled, water was added thereto, and the mixture was extracted three times with chloroform. The extraction product was washed with saturated brine, dehydrated over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (hexane:ethyl acetate=1:1), and thus 59.4 mg (75.7%) of ethyl (2S,4S)-1-acetyl-2-methyl-4-(4-morpholinophenoxy)-1,2,3,4-tetrahydroquinoline-6-carboxylate was obtained as a pale yellow oily substance.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 14 hours
  3. customAfter completion of the reaction
  4. customthe reaction liquid
  5. temperaturewas cooled
  6. extractionthe mixture was extracted three times with chloroform
  7. washThe extraction product was washed with saturated brine
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified

Sources & evidence

ORD record
ord-b1ccaf7f5d964c7e9a96255c9afcce4d
Source dataset
uspto-grants-2014_07
Patent number
US08791090B2

Reaction notes

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