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Triethylamine → 1-Benzyl-1,2,3,4-tetrahydroquinolin-7-yl 2-methylphenylcarbamate

HRID 1843284
ノート
印刷プレビュー

反応式

HRID 1843284 の反応式
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26]1([CH3:35])[C:27]([N:32]=[C:33]=[O:34])=[CH:28][CH:29]=[CH:30][CH:31]=1>ClCCl>[CH3:35][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:33](=[O:34])[O:18][C:15]1[CH:16]=[C:17]2[C:12]([CH2:11][CH2:10][CH2:9][N:8]2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:14]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 691942-Tolyl isocyanateHCID 218649361-Benzyl-1,2,3,4-tetrahydroquinolin-7-ol

生成物 1

HCID 601633901-Benzyl-1,2,3,4-tetrahydroquinolin-7-yl 2-methylphenylcarbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
35 °C

実験手順

A mixture of 1-benzyl-1,2,3,4-tetrahydroquinolin-7-ol (550 mg, 2.30 mM) and triethylamine (0.4 mL) in dry dichloromethane (DCM, 10 mL) was stirred for half an hour under nitrogen atmosphere at room temperature (35° C.). To the stirred reaction mixture, o-tolyl isocyanate (428 mg/ml, 3.45 mM) was added at once and then the reaction mixture was further stirred for 72 hours under N2 atmosphere at RT. The reaction mixture was concentrated under vacuum and then was added distilled water (15 mL) followed by the extraction with ether (3×15 mL). The ether layer was dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was finally chromatographed using chloroform-hexane (1:9) to give 8a as colorless oil. Yield: 700 mg, 81.78%.

後処理

  1. additionwas added at once and then the reaction mixture
  2. stirringwas further stirred for 72 hours under N2 atmosphere at RT
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additionwas added
  5. distillationdistilled water (15 mL)
  6. extractionfollowed by the extraction with ether (3×15 mL)
  7. dry with materialThe ether layer was dried over sodium sulphate
  8. concentrationconcentrated under vacuum
  9. customto afford the crude product, which
  10. customwas finally chromatographed

出典と根拠

ORDレコード
ord-51bf201873664e67ba6a1250fb409bbc
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946261B2

反応ノート

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