Triethylamine → HCID 18630938、化合物

HRID 1059694ノート

反応式

HRID 1059694 の反応式
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][CH2:6][CH2:7][CH2:8]OS(C)(=O)=O)=[O:4].Cl.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH2:25][CH2:26][NH:27][CH2:28][CH:29]=2)=[CH:20][CH:19]=1.C(N(CC)CC)C>C(O)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH2:29][CH2:28][N:27]([CH2:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[C:2]([F:15])([F:14])[F:1])[CH2:26][CH:25]=2)=[CH:20][CH:19]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27236124-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridinium chlorideHCID 86585100HCID 86585100、化合物

生成物 1

HCID 18630938HCID 18630938、化合物収率 45%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Methanesulfonic acid 3-(2,2,2-trifluoroacetylamino)-propyl ester (4.51 g, 18.10 mmol), 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (4.20 g, 18.25 mmol) and triethylamine (5.6 mL, 40.2 mmol) in ethanol (100 mL) were refluxed for 18 hours. The mixture was concentrated, redissolved in ethyl acetate and washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate and concentrated on to silica gel. Flash chromatography using first an ethyl acetate/hexanes gradient followed by 3% methanol/ethyl acetate gave N-{3-[4-(4-chloro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-2,2,2-trifluoro-acetamide (2.82 g, 45%) as a white solid. Mp. 105-107° C.; NMR CDCl3 δ 9.58 (br s, 1H), 7.27-7.24 (m, 4H), 6.01-5.98 (m, 1H), 3.49 (g, J=5.3 Hz, 2H), 3.20-3.17 (m, 2H), 2.77 (t, J=5.7 Hz, 2H), 2.73-2.69 (m, 2H), 2.55-2.51 (m, 2H), 1.80 (p, J=3.6 Hz, 2H); 13C NMR CDCl3 δ 138.80, 134.41, 133.15, 128.52, 126.22, 120.99, 57.72, 52.80, 50.15, 40.96, 27.61, 23.23; IR (KBr) 3300, 3099, 2981, 2953, 2925, 2907, 2810, 2758, 2734, 1695, 1558, 1494, 1469, 1444, 1352, 1184, 1137, 1118, 1097,801,722,692.

後処理

  1. concentrationThe mixture was concentrated
  2. dissolutionredissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated on to silica gel

出典と根拠

ORDレコード
ord-47643a515a2c49ed80632c80b9a9461a
出典データセット
uspto-grants-2003_02
特許番号
US06521630B1

反応ノート

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