Dimethylformamide → 1-(Cyclopropylmethyl)-5-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

HRID 851143ノート

反応式

HRID 851143 の反応式
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH2:11][NH:12][CH2:13][CH2:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:28][CH:29]1[CH2:31][CH2:30]1>O>[CH:29]1([CH2:28][N:12]2[CH2:13][CH2:14][CH:15]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH3:2])[CH:5]=3)[CH2:11]2)[CH2:31][CH2:30]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 80013(Chloromethyl)cyclopropaneHCID 130667493-(3-Methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride

生成物 1

HCID 205026391-(Cyclopropylmethyl)-5-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

A mixture of 10 g of 3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride, 100 ml of dimethylformamide, 14 g of sodium carbonate and 4.4 ml of chloromethyl cyclopropane was heated at 75° C. for 24 hours and was then cooled and diluted with water. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-1-1 cyclohexane-chloroform-triethylamine mixture to obtain 9.25 g of 1-cyclopropylmethyl-3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine.

後処理

  1. temperaturewas then cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with water
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washwas eluted with an 8-1-1 cyclohexane-chloroform-triethylamine mixture

出典と根拠

ORDレコード
ord-5f217856cc504a97a0c0949a12d5c889
出典データセット
uspto-grants-1983_05
特許番号
US04382942

反応ノート

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