HCID 57565297, compound → HCID 57565299, compound

HRID 1172174Notes

Reaction equation

HRID 1172174 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([S:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[N:23](C(=O)C)[CH2:22][CH2:21]4)(=[O:17])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1>O1CCOCC1>[F:30][C:2]([F:1])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([S:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[NH:23][CH2:22][CH2:21]4)(=[O:16])=[O:17])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 57565297HCID 57565297, compound

Product 1

HCID 57565299HCID 57565299, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-{5-[4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-2,3-dihydro-indol-1-yl}-ethanone was refluxed in 1,4-dioxane (5 mL) and concentrate HCl (2.5 mL) for 2 h. The reaction was then diluted with dichloromethane and washed with 1N HCl, saturated sodium bicarbonate, dried (Na2SO4), filtered and concentrated to provide 5-[4-(4-trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-2,3-dihydro-1H-indole (1.03 g, 75%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.48-7.20 (m, 4H). 6.88 (d, 2H), 6.60 (d, 1H), 3.70 (t, 2H), 3.36-3.33 (m, 4H), 3.15-3.12 (m, 4H), 3.10 (t, 2H).

Workup

  1. concentrationconcentrate HCl (2.5 mL) for 2 h
  2. additionThe reaction was then diluted with dichloromethane
  3. washwashed with 1N HCl, saturated sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8ee83efb29ec4a629152e9ca2632a534
Source dataset
uspto-grants-2010_11
Patent number
US07834004B2

Reaction notes

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