Diisopropylethylamine → 1-(Chroman-3-ylmethyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester

HRID 1196001

반응식

HRID 1196001 반응식
Br.[CH3:2][O:3][C:4]([C:6]1[CH2:7][NH:8][CH2:9][CH2:10][CH:11]=1)=[O:5].C(N(C(C)C)C(C)C)C.C1(C)C=CC(S(O[CH2:31][CH:32]2[CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[O:34][CH2:33]2)(=O)=O)=CC=1>CN(C)C=O>[CH3:2][O:3][C:4]([C:6]1[CH2:7][N:8]([CH2:31][CH:32]2[CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[O:34][CH2:33]2)[CH2:9][CH2:10][CH:11]=1)=[O:5]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 11267124Toluene-4-sulfonic acid Chroman-3-ylmethyl esterHCID 15560296Guvacoline Hydrobromide

생성물 1

HCID 148384031-(Chroman-3-ylmethyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester수율 83%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

First 5.55 g (25 mmol) of 1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester hydrobromide (guvacoline hydrobromide) and then 11.31 g (87.5 mmol) of N-ethyl-N,N-diisopropylamine are added to a solution of 7.96 g (25 mmol) of 3-(p-toluenesulphonyloxymethyl)chroman in 100 ml of dimethylformamide. The mixture is stirred for 15 hours at 50° and then concentrated by evaporation under a high vacuum. Water is added to the residue and extraction is carried out with diethyl ether. The organic phases are washed with water and extracted with 2N hydrochloric acid. The hydrochloric acid extracts are combined, rendered alkaline, while cold, with sodium hydroxide solution (30% strength) and extracted with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated by evaporation in vacuo. 5.92 g (83%) of 1-(chroman-3-ylmethyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester are obtained in the form of a pale yellow oil. The 1-(chroman-3-ylmethyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester hydrochloride produced therefrom using hydrochloric acid in diethyl ether melts at 158°-159° after crystallisation from methanol/diethyl ether.

후처리

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

출처 및 근거

ORD 기록
ord-8e77607c08d94c2ca13b0b4aa720a0d7
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05112855

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