Acetic Acid → cis-2-(4-Pyridylethyl)-3a,4,7,7a-tetrahydroisoindoline

HRID 1654655

反応式

HRID 1654655 の反応式
[CH2:1]1[C@@H:9]2[C@@H:4]([CH2:5][CH:6]=[CH:7][CH2:8]2)[CH2:3][NH:2]1.[CH:10]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)=[CH2:11].C(O)(=O)C>CO>[N:15]1[CH:16]=[CH:17][C:12]([CH2:10][CH2:11][N:2]2[CH2:3][C@H:4]3[C@H:9]([CH2:8][CH:7]=[CH:6][CH2:5]3)[CH2:1]2)=[CH:13][CH:14]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 75024-VinylpyridineHCID 16765331cis-2,3,3a,4,7,7a-Hexahydro-1h-isoindole

生成物 1

HCID 70072088cis-2-(4-Pyridylethyl)-3a,4,7,7a-tetrahydroisoindoline

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 0.64 g of cis-3a,4,7,7a-tetrahydroisoindoline, 0.6 mL of 4-vinylpyridine, 0.4 mL of acetic acid and 10 mL of methanol was heated under reflux for 16 hours. Removal of the solvent and short-path distillation of the residue (160° bath temperature, 0.002 mm) gave 0.74 g. of cis-2-(4-pyridylethyl)-3a,4,7,7a-tetrahydropyridine. 1H NMR (in CDCl3) δ8.5 (d, 2H); 7.1 (d, 2H); 5.8 (m, 2H); 3.0 (m, 2H); 2.7-2.8 (m, 4H); 2.4 (m, 2H); 2.2-2.3 (m, 4H) and 1.9 (d, 2H). The dihydrochloride hemi-hydrate had an indefinite melting point after crystallization from 2-propanol. Anal. Calcd. for C15H22Cl2N2.1/2H2O: C, 58.07; H, 7.47; N, 9.03. Found: C, 58.27; H, 7.47; N, 9.15.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customRemoval of the solvent and short-path distillation of the residue (160° bath temperature, 0.002 mm)
  4. customgave 0.74 g
  5. customafter crystallization from 2-propanol

出典と根拠

ORDレコード
ord-cbbe2367a11c43acac1e203fa7a2ddb2
出典データセット
uspto-grants-1995_04
特許番号
US05409929

関連ノート

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