Isopropylamine → HCID 86680969、化合物

HRID 331524

反応式

HRID 331524 の反応式
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)(=O)[CH3:2].[CH:15]([NH2:18])([CH3:17])[CH3:16].[OH-].[Na+]>ClCCl.C(OCC)C.Cl[Ti](Cl)(Cl)Cl>[CH:15]([N:18]=[C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)[CH3:2])([CH3:17])[CH3:16]

参加物

7

反応物 3

HCID 6363IsopropylamineHCID 14798Sodium HydroxideHCID 600911Ethyl 4-acetylbenzoate

生成物 1

HCID 86680969HCID 86680969、化合物

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 3283Diethyl Ether溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

Tetrachlorotitanium (16.85 mL of 1 M, 16.85 mmol) in dichloromethane was added to a solution of ethyl 4-acetylbenzoate (5.4 g, 28.09 mmol) and isopropyl amine (6.644 g, 9.657 mL, 112.4 mmol) in diethyl ether (100 mL) at 0° C. and the reaction mixture allowed to warm to ambient temperature over 15 hours. The reaction mixture was poured into a biphasic mixture of aqueous 0.5 M sodium hydroxide and diethyl ether (4:1, 150 mL) and the layers separated. The aqueous phase was extracted with diethyl ether (×2) and the combined organic phases dried (MgSO4/K2CO3 10:1), filtered and concentrated in vacuo to give ethyl 4-(1-(isopropylimino)ethyl)benzoate as a pale yellow oil (6.7 g, quantitative). 1H NMR (400.0 MHz, DMSO-d6) δ 1.15 (d, J=6.3 Hz, 6H), 1.33 (t, J=7.2 Hz, 3H), 2.25 (s, 3H), 3.88 (sept, 1H), 4.33 (q, J=7.1 Hz, 2H) and 7.91-7.97 (m, 4H) ppm; LC/MS m/z 234.2 [M+H]+.

後処理

  1. customthe layers separated
  2. extractionThe aqueous phase was extracted with diethyl ether (×2)
  3. dry with materialthe combined organic phases dried (MgSO4/K2CO3 10:1)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3fbc87f4947e4ddda1920a18c9d6828e
出典データセット
uspto-grants-2014_11
特許番号
US08877759B2

関連ノート

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