Sodium Iodide → 4-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1452473Notes

Reaction equation

HRID 1452473 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16](Cl)[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>O.C(#N)C>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([CH:16]2[C:17]3[C:12](=[CH:11][C:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])=[CH:19][CH:18]=3)[CH2:13][CH2:14][CH2:15]2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 575267806-Benzenesulfonyl-1-chloro-1,2,3,4-tetrahydro-naphthalene

Product 1

HCID 575267814-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-piperazine-1-carboxylic acid tert-butyl esterYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

6-Benzenesulfonyl-1-chloro-1,2,3,4-tetrahydro-naphthalene (0.6 g, 1.96 mmol), piperazine 1-carboxylic acid tert-butyl ester (0.65 g, 3.5 mmol), sodium iodide (0.1 g) and potassium carbonate (0.5 g) were added to 50 mL of acetonitrile, and the reaction mixture was refluxed for 120 hours. The reaction mixture was cooled and diluted with 200 mL of water. The aqueous mix was extracted twice with 200 mL of EtOAc, and the combined organic layers were washed with water, brine, and dried over MgSO4. Solvent was removed under reduced pressure, and the resulting oil was eluted through silica gel (medium pressure chromatography) eluting with EtOAc/Hexanes 20%/80%. Removal of solvent under reduced pressure afforded 0.4 g (0.88 mmol, 45%) of 4-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-piperazine-1-carboxylic acid tert-butyl ester as an oil. MS: 458 (M+H)+.

Workup

  1. temperaturethe reaction mixture was refluxed for 120 hours
  2. temperatureThe reaction mixture was cooled
  3. additionThe aqueous mix
  4. extractionwas extracted twice with 200 mL of EtOAc
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried over MgSO4
  7. customSolvent was removed under reduced pressure
  8. washthe resulting oil was eluted through silica gel (medium pressure chromatography)
  9. washeluting with EtOAc/Hexanes 20%/80%
  10. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-a38cf825c7c94d5b9b483abe0fe9f32c
Source dataset
uspto-grants-2009_01
Patent number
US07473690B2

Reaction notes

Loading…