Sodium Carbonate → HCID 68708429, compound

HRID 1818795Notes

Reaction equation

HRID 1818795 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:6]1(=[O:21])=[O:20].[C:22]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[O:20]=[S:6]1(=[O:21])[N:5]([CH2:4][CH2:3][CH2:2][N:32]2[CH2:31][CH2:30][N:29]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:34][CH2:33]2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 68709668HCID 68709668, compound

Product 1

HCID 68708429HCID 68708429, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-(3-bromopropyl)-3-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (prepared in an analogous manner as described in general procedure V), 1-Boc-piperazine (624 mg, 3.35 mmol, 6 equiv.), sodium carbonate (granular, 355 mg, 3.35 mmol, 6 equiv.), and ethanol (5 mL) in a sealed reaction vessel was heated at 90° C. for 8 h. After cooling, solid sodium carbonate was removed by decantation, and the supernatant was concentrated and re-dissolved in ethyl acetate (15 mL). The resulting solution was washed with water, dried (anhydrous sodium sulfate), and concentrated. The crude oil was pre-adsorbed onto Florisil and purified via Isco flash column chromatography (4-g redisep silica gel column, 5-60% ethyl acetate/hexane) to give 252 mg (96%) of tert-butyl 4-[3-(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)propyl]piperazine-1-carboxylate as a viscous, brown liquid. MS (ESI) m/z 473.1 ([M+H]+).

Workup

  1. customprepared in an analogous manner
  2. customin a sealed reaction vessel
  3. temperatureAfter cooling
  4. customsolid sodium carbonate was removed by decantation
  5. concentrationthe supernatant was concentrated
  6. dissolutionre-dissolved in ethyl acetate (15 mL)
  7. washThe resulting solution was washed with water
  8. dry with materialdried (anhydrous sodium sulfate)
  9. concentrationconcentrated
  10. custompurified via Isco flash column chromatography (4-g redisep silica gel column, 5-60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-63e56f7d62c344219f9fd6d5bbc13570
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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