Sodium Hydroxide → 1-(Benzyloxy)but-3-en-2-amine hydrochloride

HRID 595327ノート

反応式

HRID 595327 の反応式
[CH2:1]([O:8][CH2:9][CH:10]([NH:13]C(=O)C(Cl)(Cl)[Cl:16])[CH:11]=[CH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O>[ClH:16].[CH2:1]([O:8][CH2:9][CH:10]([NH2:13])[CH:11]=[CH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 13416079N-[1-(Benzyloxy)but-3-en-2-yl]-2,2,2-trichloroacetamide

生成物 1

HCID 135179031-(Benzyloxy)but-3-en-2-amine hydrochloride

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A mixture of N-[1-(benzyloxy)but-3-en-2-yl]-2,2,2-trichloroacetamide (7.5 g, 23 mmol) and sodium hydroxide (4.0 M in H2O, 40 mL, 160 mmol) was stirred and heated to 80° C. for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with ethyl acetate. The organic layer was separated and extracted with hydrochloric acid (2N). The aqueous layer was concentrated under reduced pressure to afford 1-(benzyloxy)but-3-en-2-amine hydrochloride. MS ESI calc'd. for C11H16NO [M+H]+ 178. found 178. 1H NMR (400 MHz, DMSO-d6) δ 8.38 (s, 2H), 7.37-7.28 (m, 5H), 5.89-5.80 (m, 1H), 5.44-5.32 (m, 2H), 4.57-4.50 (m, 2H), 3.99 (s, 1H), 3.62-3.55 (m, 2H).

後処理

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. extractionextracted with hydrochloric acid (2N)
  5. concentrationThe aqueous layer was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-cfa7854ff5cf46228c219b7efc94e6d1
出典データセット
uspto-grants-2016_01
特許番号
US09242984B2

反応ノート

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