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

HRID 595327노트

반응식

HRID 595327 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cfa7854ff5cf46228c219b7efc94e6d1
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242984B2

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