Triethylamine → HCID 57180662, compound

HRID 1857489Notes

Reaction equation

HRID 1857489 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:18][CH:19]=2)[C:14](=O)[CH2:13][CH:12]1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:34][C:35]([F:49])([F:48])[C:36]1[CH:37]=[C:38]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[CH2:39][NH2:40].C(=O)([O-])[O-].[K+].[K+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl.O>[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:18][CH:19]=2)[C:14](=[N:40][CH2:39][C:38]2[CH:41]=[C:42]([C:44]([F:45])([F:46])[F:47])[CH:43]=[C:36]([C:35]([F:34])([F:48])[F:49])[CH:37]=2)[CH2:13][CH:12]1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 57249145HCID 57249145, compound

Product 1

HCID 57180662HCID 57180662, compoundYield 119.6%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-Methyl-4-oxo-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (5.5 g, 15.1 mmol) was combined with triethylamine (15 mL, 106 mmol) and 3,5-bis-trifluoromethyl-benzylamine (5.5 g, 22.7 mmol) in anhydrous dichloromethane (80 mL). This solution was cooled in a room temperature water bath as 7.6 mL of 1M solution of titanium tetrachloride (TiCl4) in dichloromethane (7.6 mmol) was slowly added. The reaction was stirred at room temperature overnight before the mixture was poured into a stirred solution of water (125 mL) and potassium carbonate (15 g). After filtration of the resulting emulsion, the filtrate was extracted with ethyl acetate (1×200 mL, then 2×75 mL), the combined organic phases were washed with water (100 mL), brine (50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give the title product (10.63 g, >theory). 1H NMR (CDCl3) δ 1.2 (d, 3H), 2.7-2.9 (m, 2H), 4.0-4.1 (m, 1H), 4.65 (d, 1H), 4.75 (d, 1H), 5.1-5.4 (m, 2H), 7.3-7.5 (m, 5H).

Workup

  1. additionwas slowly added
  2. filtrationAfter filtration of the resulting emulsion
  3. extractionthe filtrate was extracted with ethyl acetate (1×200 mL
  4. wash2×75 mL), the combined organic phases were washed with water (100 mL), brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34cd9387e4a245378f0af80859bfa5c6
Source dataset
uspto-grants-2000_11
Patent number
US06147090

Reaction notes

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