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

HRID 1196001

反応式

HRID 1196001 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8e77607c08d94c2ca13b0b4aa720a0d7
出典データセット
uspto-grants-1992_05
特許番号
US05112855

関連ノート

読み込み中…