Sodium Hydroxide → HCID 21963089, compound

HRID 1375433Notes

Reaction equation

HRID 1375433 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C([N:18]1[C:26]2[C:21](=[CH:22][C:23]([S:27](Cl)(=[O:29])=[O:28])=[CH:24][CH:25]=2)[CH2:20][CH2:19]1)=O.[OH-].[Na+]>ClCCl>[NH:18]1[C:26]2[C:21](=[CH:22][C:23]([S:27]([N:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]3)(=[O:29])=[O:28])=[CH:24][CH:25]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 110883061-(Trifluoroacetyl)-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 21963089HCID 21963089, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl-1-piperazinecarboxylate (5.94 g, 31.9 mmol, 2.00 equiv) was added to a solution of 1-(trifluoroacetyl)indoline-5-sulfonyl chloride (1-6, 5.00 g, 15.9 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 resulting tan-colored solid dried in vacuo. A solution of the solid in a mixture of 1,4-dioxane (100 mL) and methanol (30 mL) was treated with aqueous 1N NaOH solution (47.9 mL, 47.9 mmol, 3.00 equiv), and the resulting mixture was stirred for 1 hour. The mixture was concentrated, and the resulting solid suspended in diethyl ether (130 mL) and filtered. The filtered solid was then partitioned between aqueous saturated sodium chloride solution (150 mL) and ethyl acetate (4×85 mL). The organic layer was dried over sodium sulfate and concentrated to provide the tert-butyl 4-(2,3-dihydro-1H-indol-5-ylsulfonyl)piperazine-1-carboxylate (2-1) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 7.41 (m, 2H), 6.57 (d, 1H, J=8.9 Hz), 3.69 (t, 2H, J=8.6 Hz), 3.50 (t, 2H, J=4.9 Hz), 3.09 (t, 2H, J=8.6 Hz), 2.93 (t, 2H, J=4.9 Hz) 1.42 (s, 9H).

Workup

  1. concentrationThe brown-colored reaction mixture was concentrated
  2. customthe resulting tan-colored solid dried in vacuo
  3. additionA solution of the solid in a mixture of 1,4-dioxane (100 mL) and methanol (30 mL)
  4. stirringthe resulting mixture was stirred for 1 hour
  5. concentrationThe mixture was concentrated
  6. filtrationfiltered
  7. customThe filtered solid was then partitioned between aqueous saturated sodium chloride solution (150 mL) and ethyl acetate (4×85 mL)
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2a74c4ca4359482aabf61374355caf2e
Source dataset
uspto-grants-2007_01
Patent number
US07169788B2

Reaction notes

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