Quinuclidine, 3-amino-, dihydrochloride → N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-propoxybenzamide hydrochloride

HRID 364631

반응식

HRID 364631 반응식
Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].[CH2:23]([O:26][C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29]([Cl:31])=[O:30])[CH2:24][CH3:25]>C(=O)=O.C(Cl)Cl>[ClH:31].[N:6]12[CH2:11][CH2:10][CH:9]([CH2:8][CH2:7]1)[CH:4]([NH:3][C:29](=[O:30])[C:28]1[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=1[O:26][CH2:23][CH2:24][CH3:25])[CH2:5]2

참가 물질

6

반응물 3

HCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 159219132-Propoxybenzoyl chlorideHCID 17749109Barium hydroxide, octahydrate

생성물 1

HCID 13630995N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-propoxybenzamide hydrochloride

시약·촉매·용매 2

HCID 280Carbon Dioxide용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 3.82 g (0.0192 mole) of 3-amino quinuclidine dihydrochloride in about 25 ml of carbon dioxide-free water was added 8 g (0.025 mole) of barium hydroxide octahydrate. The mixture was warmed for 5 minutes and then dried to a powder on a rotary evaporator. While protecting from contamination with carbon dioxide in the atmosphere, the powder was extracted in sequence with hot benzene and a 1:1 mixture of benzene-methylene chloride solution. The combined extracts were dried over magnesium sulfate and the mixture filtered. To the filtrate with agitation was added dropwise a solution of 3.4 g (0.0171 mole) of 2-propoxybenzoyl chloride in 50 ml of methylene chloride. The mixture was warmed on a steam bath to evaporate about 75% of the methylene chloride. Ligroin (60-110) was added and the mixture solidified. The solid was recrystallized from anhydrous ethyl alcohol to give 3.9 g (62.0%), m.p. 210°-211° C.

후처리

  1. temperatureThe mixture was warmed for 5 minutes
  2. customdried to a powder on a rotary evaporator
  3. extractionthe powder was extracted in sequence with hot benzene
  4. additiona 1:1 mixture of benzene-methylene chloride solution
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationthe mixture filtered
  7. temperatureThe mixture was warmed on a steam bath
  8. customto evaporate about 75% of the methylene chloride
  9. additionLigroin (60-110) was added
  10. customThe solid was recrystallized from anhydrous ethyl alcohol
  11. customto give 3.9 g (62.0%), m.p. 210°-211° C.

출처 및 근거

ORD 기록
ord-81f0bb67da134b038e581120492cf50b
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04605652

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