Diisopropylethylamine → 4-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidine-1-carbonitrile

HRID 1622225노트

반응식

HRID 1622225 반응식
[CH2:1]([N:3](C(C)C)C(C)C)C.[CH3:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]3[O:27][CH:26]([CH:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[CH2:25][C:24]=3[CH:34]=2)=[CH:16][CH:15]=1)(=[O:13])=[O:12].Cl.C(N(C(C)C)C(C)C)C>ClCCl.O1CCCC1.O.C(OCC)(=O)C>[CH3:10][S:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]=[CH:22][C:23]3[O:27][CH:26]([CH:28]4[CH2:33][CH2:32][N:31]([C:1]#[N:3])[CH2:30][CH2:29]4)[CH2:25][C:24]=3[CH:34]=2)=[CH:18][CH:19]=1)(=[O:12])=[O:13]

참가 물질

8

반응물 3

HCID 81531DiisopropylethylamineHCID 10997398Ethylbis(propan-2-yl)amine hydrochlorideHCID 679732894-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidine

생성물 1

HCID 866756724-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidine-1-carbonitrile

시약·촉매·용매 4

HCID 962Water용매2회HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Ethyldiisopropylamine (0.96 mL) and bromonitirile (175 mg) are added to a solution of 4-[5-(4-methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine (400 mg) in dichloromethane (10 mL) and tetrahydrofuran (10 mL), and the reaction mixture is stirred over night at room temperature. Dichloromethane and water are added and the organic phase is separated and washed with water, 10% NH4Cl solution, and brine, and dried over MgSO4. The solvent is evaporated and the residue is triturated with diethyl ether to give a brownish solid. Since this material still contains ethyldiisopropylamine hydrochloride, ethyl acetate and water are added. The organic phase is separated, dried over MgSO4 and concentrated in vacuo. The residue is again triturated with diethyl ether to afford the title compound. LC (method 2): tR=1.18 min; Mass spectrum (ESI+): m/z=383 [M+H]+.

후처리

  1. customthe organic phase is separated
  2. washwashed with water, 10% NH4Cl solution, and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent is evaporated
  5. customthe residue is triturated with diethyl ether
  6. customto give a brownish solid
  7. customThe organic phase is separated
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue is again triturated with diethyl ether

출처 및 근거

ORD 기록
ord-1c4b05e560cb4bbaa14df86876005651
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778926B2

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