Ammonia → N-(2-aminocarbonylethyl)-N-[2-(chroman-3-yl)ethyl]amine hydrochloride

HRID 1032443노트

반응식

HRID 1032443 반응식
[ClH:1].[O:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:17]([O:19]C)=O)[CH2:3]1.[NH3:21].Cl>C(O)(C)C>[ClH:1].[NH2:21][C:17]([CH2:16][CH2:15][NH:14][CH2:13][CH2:12][CH:4]1[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[O:2][CH2:3]1)=[O:19]

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 14838449N-[2-(chroman-3-yl)ethyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride

생성물 1

HCID 67907133N-(2-aminocarbonylethyl)-N-[2-(chroman-3-yl)ethyl]amine hydrochloride

시약·촉매·용매 1

HCID 3776Isopropanol용매2회

실험 절차

3 g (100 mmol) of N-[2-(chroman-3-yl)ethyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride (example 4) are added to 20 ml of 5.5N methanolic ammonia solution. The mixture is stirred in a bomb tube for 12 hours at 60°. Subsequently, the reaction mixture is concentrated by evaporation, the resulting residue is dissolved in 2N hydrochloric acid, and the acidic solution is extracted with diethyl ether. The acidic aqueous phase is rendered alkaline with 2N sodium hydroxide solution and extracted with diethyl ether. The combined ethereal phases are washed in succession with water and saturated sodium chloride solution, dried over magnesium sulfate, and concentrated by evaporation, yielding the crude base in the form of an oil. The crude base is dissolved in a small amount of isopropanol. Ethereal hydrochloric acid is added to the isopropanol solution until the mixture gives a weakly acidic reaction. The precipitate is filtered off and recrystallized from isopropanol/diethyl ether, yielding 0.6 g of N-(2-aminocarbonylethyl)-N-[2-(chroman-3-yl)ethyl]-amine hydrochloride melting at 220° to 222°.

후처리

  1. concentrationSubsequently, the reaction mixture is concentrated by evaporation
  2. dissolutionthe resulting residue is dissolved in 2N hydrochloric acid
  3. extractionthe acidic solution is extracted with diethyl ether
  4. extractionextracted with diethyl ether
  5. washThe combined ethereal phases are washed in succession with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated by evaporation
  8. customyielding the crude base in the form of an oil
  9. customgives
  10. customa weakly acidic reaction
  11. filtrationThe precipitate is filtered off
  12. customrecrystallized from isopropanol/diethyl ether

출처 및 근거

ORD 기록
ord-04de26fcbba447a2874c8c3ee4e0e76f
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04957928

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