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

HRID 1622225ノート

反応式

HRID 1622225 の反応式
[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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-1c4b05e560cb4bbaa14df86876005651
出典データセット
uspto-grants-2014_07
特許番号
US08778926B2

反応ノート

読み込み中…