반응 #41208

ord-8ca57d439fb34165987b64e0ae661fb3

반응 방정식

COC(=O)CC(C)N1CCN(c2ccc(O)cc2)CC1
compound
COC(=O)CC(C)N1CCN(c2ccc(O)cc2)CC1
3-[4-(4-Hydroxy-phenyl)-piperazin-1-yl]-butyric acid methyl ester
O=C([O-])[O-].[K+].[K+]
K2CO3
C#CCBr
3-bromopropyne
C#CCOc1ccc(N2CCN(CCC(=O)OC)CC2)cc1
title compound
수율 39.7%
C#CCOc1ccc(N2CCN(CCC(=O)OC)CC2)cc1
3-[4-(4-Prop-2-ynyloxy-phenyl)-piperazin-1-yl]-propionic acid methyl ester
수율 39.7%

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타partitioned between water and ethyl acetate
  2. 2
    세척washed with brine
  3. 3
    건조dried over anhydrous Na2SO4
  4. 4
    기타evaporated under vacuum
  5. 5
    기타to give a brown oil
  6. 6
    기타The crude product was purified by silica gel flash chromatography (30% ethyl acetate in hexane)

실험 절차

To a mixture of the compound from step 1 (278 mg, 1.0 mmol) and K2CO3 (152 mg, 1.1 mmol) in DMF (5 mL) was added 3-bromopropyne (130 mg, 1.1 mmol) dropwise at rt. The reaction mixture was stirred at rt overnight and then partitioned between water and ethyl acetate. The organic payers were combined and washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum to give a brown oil. The crude product was purified by silica gel flash chromatography (30% ethyl acetate in hexane) to furnish the title compound (120 mg, 38%) as a light yellow solid; MS; m/z 317 (M+H).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07728032B2uspto-grants-2010_06