Amantadine → N-(Adamantan-1-yl)prop-2-enimidic acid

HRID 1748696

반응식

HRID 1748696 반응식
[C:1]12([NH2:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>C1COCC1>[C:1]12([NH:11][C:19](=[O:22])[CH:20]=[CH2:21])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

참가 물질

5

반응물 3

HCID 2130AmantadineHCID 8471TriethylamineHCID 13140Acryloyl chloride

생성물 1

HCID 284637N-(Adamantan-1-yl)prop-2-enimidic acid수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1-Adamantylamine (0.76 g; 5.0 mmol) and triethylamine (0.77 ml; 5.5 mmol) were dissolved in dry THF (40 mL) on an ice bath. After dropping acryloyl chloride (0.45 ml; 5.5 mmol) onto the solution, the mixture was stirred for 4 hours. After the reaction, the precipitate was removed by filtration, and the supernatant liquid was concentrated under reduced pressure. The resulting crude product was recrystallized from chloroform to give N-(1-adamantyl)acrylamide (0.85 mg; yield: 83%).

후처리

  1. customAfter the reaction
  2. customthe precipitate was removed by filtration
  3. concentrationthe supernatant liquid was concentrated under reduced pressure
  4. customThe resulting crude product was recrystallized from chloroform

출처 및 근거

ORD 기록
ord-f68d3521c38c43e1b183e0ec68c0dd61
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150762B2

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