Diisopropylethylamine → 1-[2-(Chroman-3-yl)ethyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester

HRID 1032398노트

반응식

HRID 1032398 반응식
Cl.[CH2:2]([O:4][C:5]([C:7]1[CH2:8][NH:9][CH2:10][CH2:11][CH:12]=1)=[O:6])[CH3:3].C(N(C(C)C)C(C)C)C.C1(C)C=CC(S(O[CH2:32][CH2:33][CH:34]2[CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[O:36][CH2:35]2)(=O)=O)=CC=1>CN(C)C=O>[CH2:2]([O:4][C:5]([C:7]1[CH2:8][N:9]([CH2:32][CH2:33][CH:34]2[CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[O:36][CH2:35]2)[CH2:10][CH2:11][CH:12]=1)=[O:6])[CH3:3]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 205700Ethyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochlorideHCID 148384153-[2-(p-Toluenesulphonyloxy)ethyl]chroman

생성물 1

HCID 148384331-[2-(Chroman-3-yl)ethyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester수율 52.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

First 2.1 g (11 mmol) of 1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester hydrochloride and then 4.53 g (35 mmol) of N-ethyl-N,N-diisopropylamine are added to a solution of 3.32 g (10 mmol) of 3-[2-(p-toluenesulphonyloxy)ethyl]chroman in 50 ml of absolute dimethylformamide. The mixture is stirred for 16 hours at 60° and, after cooling, is concentrated by evaporation under a high vacuum. Water is added to the oily residue and extraction is carried out with diethyl ether. The combined organic phases are extracted with 2N hydrochloric acid. The combined hydrochloric acid extracts are rendered alkaline, while cold, with sodium hydroxide solution (30% strength) and extracted with dichloromethane. The combined dichloromethane phases are dried over sodium sulphate and concentrated by evaporation in vacuo. 1.65 g (52.3%) of 1-[2-(chroman-3-yl)ethyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester are obtained in the form of a yellow oil. The 1-[2-(chroman-3-yl)ethyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester hydrochloride produced therefrom using hydrochloric acid in diethyl ether crystallises from acetone/diethyl ether and melts at 177°-178°.

후처리

  1. temperatureafter cooling
  2. concentrationis concentrated by evaporation under a high vacuum
  3. additionWater is added to the oily residue and extraction
  4. extractionThe combined organic phases are extracted with 2N hydrochloric acid
  5. extractionwhile cold, with sodium hydroxide solution (30% strength) and extracted with dichloromethane
  6. dry with materialThe combined dichloromethane phases are dried over sodium sulphate
  7. concentrationconcentrated by evaporation in vacuo

출처 및 근거

ORD 기록
ord-b36a7ca7905449bf889ebdbb703982c8
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04957928

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