Ammonia → (+/-)-2-Benzyl-2-(3'-dimethylaminopropoxy)-1,7,7-trimethyl-bicyclo(2,2,1) heptane

HRID 66560

반응식

HRID 66560 반응식
[NH2-].[Na+].[CH2:3]([C:10]1([OH:20])[CH2:15][CH:14]2[C:16]([CH3:18])([CH3:17])[C:11]1([CH3:19])[CH2:12][CH2:13]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N.[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26]Cl.C(O)(=O)C(C(C(O)=O)O)O.Cl.[OH-].[NH4+]>C1C=CC=CC=1.O>[CH2:3]([C:10]1([O:20][CH2:26][CH2:25][CH2:24][N:23]([CH3:28])[CH3:22])[CH2:15][CH:14]2[C:16]([CH3:17])([CH3:18])[C:11]1([CH3:19])[CH2:12][CH2:13]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

10

반응물 7

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8752,3-Dihydroxybutanedioic AcidHCID 14923Ammonium HydroxideHCID 24533Sodium amideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 2511722-Benzyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

생성물 1

HCID 13749826(+/-)-2-Benzyl-2-(3'-dimethylaminopropoxy)-1,7,7-trimethyl-bicyclo(2,2,1) heptane

시약·촉매·용매 2

HCID 241Benzene용매3회HCID 962Water용매

반응 조건

온도
30 °C

실험 절차

A suspension of 3.9 g (0.1 mole) of sodium amide in 100 ml of anhydrous benzene is heated to boiling, and a solution of 24.4 g (0.1 mole) of (±)-2-benzyl-1,7,7-trimethyl-bicyclo(2,2,1)-heptan-2-ol in 100 ml of anhydrous benzene is added dropwise, under continuous stirring. When the addition of the above solution is completed the reaction mixture is boiled until the formation of ammonia gas is ceased, and while further continuing the stirring, a solution of 13.4 g (0.11 mole) of 1-dimethylamino-3-chloro-propane in 20 ml of anhydrous benzene is added. After boiling the mixture for further 6 hours it is cooled to 30° C., washed three times with 40 ml of water each, and extracted with a solution of 15 g (0.1 mole) of tartaric acid in 50 ml of water or with 0.11 mole of diluted aqueous hydrochloric acid. The aqueous solution cooled to 0°-5° C. is made alkaline to pH 10 with concentrated ammonium hydroxide. The base separated as an oil is extracted with dichloroethane. On distilling off the solvent, the residue is fractionated in vacuo.

후처리

  1. temperatureis heated
  2. additionWhen the addition of the above solution
  3. customfor further 6 hours
  4. washwashed three times with 40 ml of water each, and
  5. temperatureThe aqueous solution cooled to 0°-5° C.
  6. customThe base separated as an oil
  7. extractionis extracted with dichloroethane
  8. distillationOn distilling off the solvent

출처 및 근거

ORD 기록
ord-138ae41e29694560a93721ec503396c0
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04342762

연결된 노트

불러오는 중…