Formaldehyde → 3-[3(S)-Ethyl 4(R)-piperidyl]-1-(6-methoxy-4-quinolyl)-1(S)-propanol

HRID 65221ノート

反応式

HRID 65221 の反応式
Cl.Cl.[CH:3]([C@@H:5]1[C@H:10]([CH2:11][CH2:12][C@@H:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)[OH:14])[CH2:9][CH2:8][NH:7][CH2:6]1)=[CH2:4].[OH-].[Na+].C=O.C1(C)C(CO)=CC=CC=1.C(NCC)C>O>[CH2:3]([C@H:5]1[C@H:10]([CH2:11][CH2:12][C@@H:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)[OH:14])[CH2:9][CH2:8][NH:7][CH2:6]1)[CH3:4]

参加物

6

反応物 4

HCID 712FormaldehydeHCID 14798Sodium Hydroxide2 回HCID 30682314-Quinolinemethanol, alpha-(2-(3-ethenyl-4-piperidinyl)ethyl)-6-methoxy-, dihydrochloride, (3R-(3-alpha,4-alpha(S*)))-HCID 70380594HCID 70380594、化合物

生成物 1

HCID 57471123-[3(S)-Ethyl 4(R)-piperidyl]-1-(6-methoxy-4-quinolyl)-1(S)-propanol

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A mixture of 6 g of 3-[3(R)-ethenyl 4(R)-piperidyl]-1-(6-methoxy-4-quinolyl)-1(S)-propanol dihydrochloride, 15 ml of a normal aqueous solution of sodium hydroxide, 1.2 ml of a 0.4% aqueous solution of formaldehyde and 60 ml of water was heated at 120° C. for 24 hours in an autoclave. After cooling, the reaction medium was made alkaline by addition of sodium hydroxide lye and extracted with methylene chloride. The organic phase was washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The oily residue obtained was subjected to high pressure liquid chromatography (support: silica gel; eluant: 100/7.5/3.75 toluene-methanol-diethylamine mixture). The separated fractions containing the desired product were evaporated. There was thus recovered 2.6 g of an oil which, by the action of HCl in ethanol, was converted into the dihydrochloride. After three recrystallizations of this last product in ethanol, 0.7 g of 3-[3(S)-ethenyl 4(R)-piperidyl]-1-(6-methoxy-4-quinolyl)-1(S)-propanol were obtained in the form of the dihydrochloride melting at 204° C.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with methylene chloride
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe oily residue obtained

出典と根拠

ORDレコード
ord-6b4936d098784889950b2ef5ce10dd93
出典データセット
uspto-grants-1986_09
特許番号
US04613607

反応ノート

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