Triethylamine → HCID 71255102, compound

HRID 540316Notes

Reaction equation

HRID 540316 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][S:14]([C:17]1[CH:18]=[CH:19][C:20]2[CH2:26][NH:25][CH2:24][CH2:23][CH2:22][C:21]=2[CH:27]=1)(=[O:16])=[O:15].C(N(CC)CC)C.CN1CCCC1=O>O>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([N:25]2[CH2:24][CH2:23][CH2:22][C:21]3[CH:27]=[C:17]([S:14]([CH3:13])(=[O:15])=[O:16])[CH:18]=[CH:19][C:20]=3[CH2:26]2)[CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 6075032,4-DichloroquinolineHCID 71255243HCID 71255243, compound

Product 1

HCID 71255102HCID 71255102, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 2,4-dichloroquinoline (126 mg, 0.637 mmol), 7-(methylsulfonyl)-2,3,4,5-tetrahydro-1H-2-benzazepine (144 mg, 0.637 mmol), triethylamine (0.106 mL, 0.765 mmol) and N-methyl-2-pyrrolidone (2 mL) was heated with stirring in a sealed tube for 4 hours at 100° C. The resulting mixture was diluted with water and extracted with ethyl acetate (15 mL×3). The organic layers were combined and washed with brine (15 mL×3), and then dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:5) to afford 55.6 mg of product as a white solid (yield was 22.5%). MS obsd. (ESI+) [(M+H)+] 387.

Workup

  1. temperaturewas heated
  2. extractionextracted with ethyl acetate (15 mL×3)
  3. washwashed with brine (15 mL×3)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:5)

Sources & evidence

ORD record
ord-f190ab8745e7446fbeceb4526dbf17ca
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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