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

HRID 875347Notes

Reaction equation

HRID 875347 reaction equation
Cl.Cl.[F:3][C:4]([F:46])([F:45])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[CH:44]=[CH:43][C:16]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][CH2:26][NH:27][CH:28]3[CH2:37][CH2:36][CH2:35][C:34]4[N:33]=[C:32]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:31]=[CH:30][C:29]3=4)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.C(N(CC)CC)C.C(OCC)(=O)C.O>C1COCC1>[F:46][C:4]([F:3])([F:45])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][C:13]2[CH:44]=[CH:43][C:16]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][CH2:26][NH:27][CH:28]3[CH2:37][CH2:36][CH2:35][C:34]4[N:33]=[C:32]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:31]=[CH:30][C:29]3=4)=[CH:15][CH:14]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86709836Ethyl 5-[(2-{2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzyl)oxy]phenyl}ethyl)amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride

Product 1

HCID 86709837Ethyl 5-[(2-{2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzyl)oxy]phenyl}ethyl)amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1045 mg (1.55 mmol) of ethyl 5-[(2-{2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzyl)oxy]-phenyl}ethyl)amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride (Enantiomer 2, Example 154A) were taken up in 15 ml of THF, 0.65 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 concentrated to dryness. This gave 800 mg (1.33 mmol, 86% 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. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-854976192c154031b113d9bd4cf428bf
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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