Indoline → HCID 57565299, compound

HRID 2110125Notes

Reaction equation

HRID 2110125 reaction equation
N1C2C(=CC=CC=2)CC1.[F:10][C:11]([F:40])([F:39])[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([S:24]([C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[N:32](C(=O)C)[CH2:31][CH2:30]4)(=[O:26])=[O:25])[CH2:20][CH2:19]2)=[CH:14][CH:13]=1>O1CCOCC1>[F:39][C:11]([F:10])([F:40])[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:19][CH2:20][N:21]([S:24]([C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[NH:32][CH2:31][CH2:30]4)(=[O:25])=[O:26])[CH2:22][CH2:23]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 10328IndolineHCID 57565297HCID 57565297, compound

Product 1

HCID 57565299HCID 57565299, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-|4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl|-2,3-dihydro-1H-indole: 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-e95efeda7e8c4840a59ade74545adb3d
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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