2-Morpholinoethanol → 2-(4-Morpholinyl)ethyl 9H-beta-carboline-3-carboxylate

HRID 992566ノート

反応式

HRID 992566 の反応式
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([O:16][CH3:17])=[O:15])[N:2]=1.OC[CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>CN(C)C1C=CN=CC=1.C1(C)C(C)=CC=CC=1>[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([O:16][CH2:17][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:15])[N:2]=1

参加物

5

反応物 2

HCID 611632-MorpholinoethanolHCID 107704Methyl 9H-pyrido(3,4-b)indole-3-carboxylate

生成物 1

HCID 98837652-(4-Morpholinyl)ethyl 9H-beta-carboline-3-carboxylate収率 64%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 7237O-Xylene溶媒

実験手順

A suspension of β-carboline-3-carboxylic acid, methyl ester (5.3 g, 23.4 mmol), 4-(2-hydroxyethyl) morpholine (4.62 g, 35 mmol), 4-dimethylaminopyridine (1.2 g, 9.8 mmol), 4 Å molecular sieves (5 g) and xylene (250 mL) was heated at reflux for 48 hours. The reaction mixture was cooled to room temperature, concentrated under vacuum, and the resulting slurry was partitioned with CH2Cl2 (250 mL). The mixture was filtered under vacuum and the residue was washed with CH2Cl2 (2×25 mL). Combined organic layers were washed several times with water, dried over Na2SO4, and concentrated. Purification of crude product by column chromatography on silica with 8% 2M NH3—CH3OH in CH2Cl2 as eluent furnished the desired product (4.8 g, 64%) as a pale yellow solid. 1H NMR (CDCl3) δ9.09 (s, 1H), 8.88 (s, 1H), 8.21 (d,J=7.9 Hz, 1H), 7.63 (d,J=8.1 Hz, 1H), 7.63 (d,J=8.1 Hz, 1H), 7.62 (t,J=7.38 (t, J=7.4 Hz, 2H), 4.63 (t, J=6.1 Hz, 2H), 3.73 (t, J=4.6 Hz, 4H), 6.1 Hz, 2H), 2.59 (t, J=4.6 Hz, 4H); MS (APCI; (M+H)+) m/z 326.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. concentrationconcentrated under vacuum
  4. customthe resulting slurry was partitioned with CH2Cl2 (250 mL)
  5. filtrationThe mixture was filtered under vacuum
  6. washthe residue was washed with CH2Cl2 (2×25 mL)
  7. washCombined organic layers were washed several times with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customPurification of crude product by column chromatography on silica with 8% 2M NH3—CH3OH in CH2Cl2 as eluent

出典と根拠

ORDレコード
ord-bb297edeab694a879cb02c4c913574f1
出典データセット
uspto-grants-2002_10
特許番号
US06469021B1

反応ノート

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