Hydrochloric Acid → 8-Morpholino-2,3-dihydrobenzo[b][1,4]dioxin-5-amine

HRID 1487203ノート

反応式

HRID 1487203 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]3[O:13][CH2:14][CH2:15][O:16][C:11]=3[C:10]([NH:17]C(=O)C)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl>CO>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]3[O:13][CH2:14][CH2:15][O:16][C:11]=3[C:10]([NH2:17])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86699687N-(8-morpholino-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acetamide

生成物 1

HCID 682847868-Morpholino-2,3-dihydrobenzo[b][1,4]dioxin-5-amine収率 60%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of N-(8-morpholino-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acetamide (2 g, 7.19 mmol) in methanol (100 mL) was added concentrated Hydrochloric acid (5 mL) and then the mixture was stirred at room temperature overnight. After the solvent was removed under reduce pressure, water was added and the pH was adjusted to 7-8 using aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate and the combined organic phases were dried over anhydrous sodium sulfate, concentrated to give a crude product, which was purified by silica gel column chromatography (petroleum ether/ethyl acetate 2/1) to afford the product 8-morpholino-2,3-dihydrobenzo[b][1,4]dioxin-5-amine (1 g, yield 60%). 1H NMR (400 MHz, CDCl3) δ ppm 6.38-6.41 (d, 1H, J=8.4 Hz), 6.27-6.29 (d, 1H, J=8.4 Hz), 4.28-4.32 (m, 4H), 3.85-3.88 (t, 4H, J=4.8 Hz), 3.55 (s, 2H), 2.95-2.97 (t, 4H, J=4.8 Hz).

後処理

  1. customAfter the solvent was removed
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe combined organic phases were dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give a crude product, which
  7. customwas purified by silica gel column chromatography (petroleum ether/ethyl acetate 2/1)

出典と根拠

ORDレコード
ord-4487b51164eb4c39886e126bac379a6b
出典データセット
uspto-grants-2016_08
特許番号
US09428508B2

反応ノート

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