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

HRID 2051543

반응식

HRID 2051543 반응식
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]12([NH2:16])[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.C(N(CC)CC)C>C(OCC)C>[C:6]12([NH:16][C:1](=[O:4])[CH:2]=[CH2:3])[CH2:13][CH:12]3[CH2:11][CH:10]([CH2:9][CH:8]([CH2:14]3)[CH2:7]1)[CH2:15]2

참가 물질

5

반응물 3

HCID 2130AmantadineHCID 8471TriethylamineHCID 13140Acryloyl chloride

생성물 1

HCID 284637N-(Adamantan-1-yl)prop-2-enimidic acid

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of acryloyl chloride (4.05 ml, 0.05 mole) in ethyl ether (25 ml) was added to a cold (+5° C.) soltuion of 1-adamantaneamine (7.65 g, 0.05 mole) and triethylamine (15.3 ml, 0.11 mole) in ethyl ether (300 ml) and the solution stirred for 72 hours at room temperature. The solvent was removed on a rotary evaporator. The residue was dissoled in ethyl acetate (100 ml), washed with 10 percent hydrochloric acid (100 ml) and water (50 ml), dried over sodium sulfate, filtered and the solvent removed in vacuo leaving an oily solid which was crystallized from methanol-ethyl acetate-hexane. The structure was confirmed by NMR.

후처리

  1. customThe solvent was removed on a rotary evaporator
  2. washwashed with 10 percent hydrochloric acid (100 ml) and water (50 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customleaving an oily solid which
  7. customwas crystallized from methanol-ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-5003ff57a4614636a966e57c8557f851
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05019597

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