Water → Ethyl 5-({2-[2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate

HRID 875338Notes

Reaction equation

HRID 875338 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[CH:43]=[CH:42][C:15]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:24][CH2:25][NH:26][CH:27]3[CH2:36][CH2:35][CH2:34][C:33]4[N:32]=[C:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:30]=[CH:29][C:28]3=4)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.C(OCC)(=O)C.O>C1COCC1>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:24][CH2:25][NH:26][CH:27]3[CH2:36][CH2:35][CH2:34][C:33]4[N:32]=[C:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:30]=[CH:29][C:28]3=4)=[CH:42][CH:43]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86709826Ethyl 5-({2-[2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride

Product 1

HCID 86709827Ethyl 5-({2-[2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3290 mg (5.58 mmol) of ethyl 5-({2-[2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}-amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride (Enantiomer 2, Example 132A) were taken up in 50 ml of THF, 3.11 ml of triethylamine were added and the mixture was stirred at room temperature for one hour. Ethyl acetate and water were then added to the reaction solution, the phases were separated and the aqueous phase was extracted once more with ethyl acetate. The combined organic phases were again washed with water, dried over magnesium sulphate, filtered and then evaporated to dryness. This gave 2150 mg (3.89 mmol, 70% of theory) of the target compound.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted once more with ethyl acetate
  3. washThe combined organic phases were again washed with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f10bee0bf9f0412fab6484ec00a60926
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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