Sodium Hydroxide → HCID 22583463, compound

HRID 1375429Notes

Reaction equation

HRID 1375429 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.FC(F)(F)C([N:12]1[C:20]2[C:15](=[CH:16][C:17]([S:21](Cl)(=[O:23])=[O:22])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)=O.[OH-].[Na+]>ClCCl.O1CCOCC1.CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:21]([C:17]2[CH:16]=[C:15]3[C:20](=[CH:19][CH:18]=2)[NH:12][CH2:13][CH2:14]3)(=[O:22])=[O:23])[CH2:4][CH2:3]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 110883061-(Trifluoroacetyl)-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 22583463HCID 22583463, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

N-Methylpiperazine (4.41 mL, 39.7 mmol, 2.00 equiv) was added to a solution of 1-(trifluoroacetyl)indoline-5-sulfonyl chloride (1-6, 6.23 g, 19.9 mmol, 1 equiv) in dichloromethane (50 mL) at 23° C., and the resulting mixture was stirred for 45 minutes. The brown-colored reaction mixture was concentrated and the residue dried in vacuo to give a tan solid. A suspension of the solid in a mixture of 1,4-dioxane (130 mL) and methanol (35 mL) was then treated with aqueous 1N NaOH solution (81.6 mL, 81.6 mmol, 3.00 equiv) and stirred for 1 hour. The mixture was concentrated, and the resulting solids were suspended in diethyl ether (175 mL), filtered, and dried in vacuo. The resulting solid was then partitioned between saturated sodium chloride solution (200 mL) and ethyl acetate (4×100 mL). The organic layer was dried over sodium sulfate and concentrated to provide the 5-[(4-methylpiperazin-1-yl)sulfonyl]indoline (1-7) as a tan solid. 1H NMR (500 MHz, DMSO-d6) δ 7.26 (s, 1H), 7.25 (d, 1H, J=7.8 Hz), 6.52 (d, 1H, 8.1 Hz), 6.48 (s, 1H), 3.55 (t, 2H, J=8.8 Hz), 3.00 (t, 2H, J=8.54 Hz), 2.79 (br s,4H), 2.34 (br s, 4H), 2.13 (s, 3H).

Workup

  1. concentrationThe brown-colored reaction mixture was concentrated
  2. customthe residue dried in vacuo
  3. customto give a tan solid
  4. additionA suspension of the solid
  5. stirringstirred for 1 hour
  6. concentrationThe mixture was concentrated
  7. filtrationfiltered
  8. customdried in vacuo
  9. customThe resulting solid was then partitioned between saturated sodium chloride solution (200 mL) and ethyl acetate (4×100 mL)
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ad8bf4f240dd4119866551966a9750a8
Source dataset
uspto-grants-2007_01
Patent number
US07169788B2

Reaction notes

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