1,5-Dibromopentane → 6-Methoxy-2-methyl-4-phenyl-3-(2-piperidin-1-ylethyl)isoquinolin-1(2H)-one hydrochloride

HRID 17860

반응식

HRID 17860 반응식
[ClH:1].[NH2:2][CH2:3][CH2:4][C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([O:21][CH3:22])=[CH:10][CH:9]=2.C(N(CC)CC)C.Br[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]Br>CC(O)(C)C>[ClH:1].[CH3:22][O:21][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:23])[N:6]([CH3:24])[C:5]([CH2:4][CH2:3][N:2]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[C:14]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 81001,5-Dibromopentane2회HCID 8471TriethylamineHCID 684337913-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride

생성물 1

HCID 684326076-Methoxy-2-methyl-4-phenyl-3-(2-piperidin-1-ylethyl)isoquinolin-1(2H)-one hydrochloride

시약·촉매·용매 1

HCID 6386tert-Butanol용매

반응 조건

온도
150 °C

실험 절차

To a solution of 3-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride (100 mg, 0.290 mmol) in 15 mL of 2-methyl-2-propanol in a pressure tube was added triethylamine (0.142 mL, 1.02 mmol), followed by 1,5-dibromopentane (0.047 mL, 0.348 mmol). The mixture was heated at 150° C. overnight. Another portion of 1,5-dibromopentane was added (0.023 mL), and the heating continued for another 24 hours. After cooling to room temperature, the mixture was concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC. The pure fractions were concentrated in vacuo, taken up in EtOAc and washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The product was taken up in dichloromethane, treated with excess ethereal HCl, and concentrated in vacuo to provide the HCl salt. Proton NMR for the product was consistent with the titled compound. ESI+MS: 377.19 [M+H]+.

후처리

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe crude residue was purified by preparative reversed phase HPLC
  4. concentrationThe pure fractions were concentrated in vacuo
  5. washwashed with saturated NaHCO3 solution and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additiontreated with excess ethereal HCl
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-de3e82e445c24748a9cfd77505e00479
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741322B2

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