Potassium Hydroxide → 4-(2-(6-methoxy-2-methyl-1H-indol-1-yl)ethyl)morpholine

HRID 574612

反応式

HRID 574612 の反応式
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[OH-].[K+].[CH3:13][O:14][C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[C:20]([CH3:24])[NH:21]2)=[CH:17][CH:16]=1>CS(C)=O>[CH3:13][O:14][C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[C:20]([CH3:24])[N:21]2[CH2:3][CH2:4][N:5]2[CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 108447096-methoxy-2-methyl-1H-indole

生成物 1

HCID 667645524-(2-(6-methoxy-2-methyl-1H-indol-1-yl)ethyl)morpholine

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

To a solution of 2-chloroethylmorpholine HCl (138 mg, 0.74 mmol) in 0.3 mL DMSO was added pulverized KOH (104 mg, 1.86 mmol), then after 10 min, a solution of 6-methoxy-2-methylindole (138 mg, 0.74 mmol) in 0.2 mL DMSO was added and the reaction stirred at room temperature overnight. The reaction mixture was partitioned between H2O and toluene, and the organic extract washed two times with H2O, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography using a gradient from 0 to 10% MeOH in CH2Cl2 to give a final yield of 17 mg (0.062 mmol). 1H NMR (500 MHz, CDCl3, δ): 2.45 (s, 3H), 2.50-2.63 (m, 4H), 2.67 (t, J=7.4 Hz, 2H), 3.71-3.83 (m, 4H), 3.90 (s, 3H), 4.18 (t, J=7.4 Hz, 2H), 6.19 (s, 1H), 6.78 (dd, J=8.5 Hz, 2.2 Hz, 1H), 6.81 (s, 1H), 7.42 (d, J=8.5 Hz, 1H). 13C NMR (500 MHz, CDCl3, δ): 12.77, 40.98, 54.13, 55.92, 57.74, 66.94, 93.50, 99.82, 108.35, 120.26, 122.51, 135.31, 137.25, 155.53. MS m/z 275.3 [M+H]+.

後処理

  1. customThe reaction mixture was partitioned between H2O and toluene
  2. extractionthe organic extract
  3. washwashed two times with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified via silica gel chromatography
  8. customto give a final yield of 17 mg (0.062 mmol)

出典と根拠

ORDレコード
ord-653b3416b18c4e5b886d1d1196b6c569
出典データセット
uspto-grants-2015_05
特許番号
US09034895B2

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