Triethylamine → 2-(3-(4-(4-Methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetonitrile

HRID 1752247ノート

反応式

HRID 1752247 の反応式
Br[CH:2]1[CH2:6][CH2:5][C:4](=[O:7])[N:3]1[CH2:8][C:9]#[N:10].Cl.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(#N)C>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([CH:22]2[CH2:27][CH2:26][N:25]([CH:5]3[CH2:6][CH2:2][N:3]([CH2:8][C:9]#[N:10])[C:4]3=[O:7])[CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:19]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27405874-(4-Methoxybenzoyl)piperidine hydrochlorideHCID 893757442-(2-Bromo-5-oxopyrrolidin-1-yl)acetonitrile

生成物 1

HCID 893757962-(3-(4-(4-Methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetonitrile収率 77.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 2-(2-bromo-5-oxopyrrolidin-1-yl)acetonitrile (730 mg, 3.6 mmol) and (4-methoxyphenyl)(piperidin-4-yl)methanone hydrochloride (920 mg, 3.6 mmol) in acetonitrile (4 mL) was added triethylamine (1.5 mL, 11 mmol). The mixture was microwave at 130° C. for 12 minutes. The solvent was removed in vacuo and the residue was taken up in methylene chloride and water. The organic layer was purified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0) to provide slightly yellow oil (950 mg, 74% yield). 1H NMR (400 MHz, CDCl3) δ 7.94 (d, J=8.5 Hz, 2H), 6.96 (d, J=8.5 Hz, 2H), 4.22-4.39 (m, 2H), 3.90 (s, 3H), 3.57 (dt, J=22.6, 9.0 Hz, 2H), 3.40-3.51 (m, J=8.5 Hz, 1H), 3.23-3.39 (br s, 1H), 2.93-3.20 (m, 3H), 2.33-2.61 (m, 2H), 2.13-2.31 (m, 1H), 1.83-2.03 (m, 4H). HRMS calculated for C13H23N3O3 342.1818. found (ESI, [M+H]+), 342.1830.

後処理

  1. customat 130° C.
  2. customfor 12 minutes
  3. customThe solvent was removed in vacuo
  4. customThe organic layer was purified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0)

出典と根拠

ORDレコード
ord-4de8130ef5d7465fb6d5ca1818822819
出典データセット
uspto-grants-2015_10
特許番号
US09163003B2

反応ノート

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