Triethylamine → 1-Boc-4-(4-ethynylphenyl)piperazine

HRID 2281809노트

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HRID 2281809 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C[Si]([C:25]#[CH:26])(C)C.CCN(CC)CC>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[C:25]([C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)#[CH:26]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 2795511Tert-butyl 4-(4-iodophenyl)piperazine-1-carboxylate

생성물 1

HCID 866588361-Boc-4-(4-ethynylphenyl)piperazine수율 96%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A microwave vial was charged with tert-butyl 4-(4-iodophenyl)piperazine-1-carboxylate (300 mg, 0.773 mmol), trimethylsilylacetylene (0.22 mL, 1.54 mmol), NEt3 (3.0 mL), DMF (1.5 mL), CuI (15 mg, 0.080 mmol), and PdCl2(PPh3)2 (27 mg, 0.039 mmol). The vial was capped and heated in the microwave at 100° C. for 1 h. After removing the NEt3 in vacuo, the residue was extracted with EtOAc (15 mL). The organic layer was then washed with NaHCO3 (sat.) (5 mL), H2O (5 mL), brine (5 mL) and then dried over MgSO4. The solvent was removed and then the material was dissolved into MeOH (4 mL) and THF (2 mL). K2CO3 (1.0 mL of a 1M solution) was added and the reaction stirred for 3 h. The solvent was removed and the residue extracted with EtOAc (15 mL). The organic layer was washed with brine (5 mL) and then dried over MgSO4. The solvent was removed and the product dried under high vacuum to give the title compound as a brown solid (212 mg, 96%); MS ESI 287.0 [M+H]+, calcd for [C17H22N2O2+H]+ 287.18.

후처리

  1. customThe vial was capped
  2. customAfter removing the NEt3 in vacuo
  3. extractionthe residue was extracted with EtOAc (15 mL)
  4. washThe organic layer was then washed with NaHCO3 (sat.) (5 mL), H2O (5 mL), brine (5 mL)
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed
  7. dissolutionthe material was dissolved into MeOH (4 mL) and THF (2 mL)
  8. additionK2CO3 (1.0 mL of a 1M solution) was added
  9. customThe solvent was removed
  10. extractionthe residue extracted with EtOAc (15 mL)
  11. washThe organic layer was washed with brine (5 mL)
  12. dry with materialdried over MgSO4
  13. customThe solvent was removed
  14. customthe product dried under high vacuum

출처 및 근거

ORD 기록
ord-2f0ec94236d043bbab724cc35f5fb141
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139563B2

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