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

HRID 1452473노트

반응식

HRID 1452473 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a38cf825c7c94d5b9b483abe0fe9f32c
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473690B2

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