Benzothiazole → [2-Benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl)methanone

HRID 1450440

反応式

HRID 1450440 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([Li])CCC.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([C:31](OC)=[O:32])[CH2:27][CH2:26]2)=[CH:19][CH:18]=1>O1CCCC1.CCCCCC>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:31]([CH:28]1[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)[CH2:26][CH2:27]1)=[O:32]

参加物

6

反応物 3

HCID 7222BenzothiazoleHCID 108695871-[2-(4-Methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl esterHCID 178418339Butyllithium

生成物 1

HCID 9842862[2-Benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl)methanone

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

Dissolve freshly distilled benzothiazole (3.41 g, 25.24 mmol) in anhydrous tetrahydrofuran (60 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, n-butyllithium (15.14 mL of a 2.5M solution in hexane, 37.86 mmol) and stir briefly at -78° C. Add, by dropwise addition, a solution of 1-[2-(4-methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl ester (7.0 g, 25.24 mmol) in anhydrous tetrahydrofuran (40 mL). Stir for 1 hour at -78° C., quench with methanol (5 mL) and pour into saturated ammonium chloride (100 mL). Filter, separate the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phases and wash with water and brine. Dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (ethyl acetate) and recrystallize (cyclohexane) to give the title compound as a pale yellow powder; mp 118°-120° C.

後処理

  1. additionAdd, by dropwise addition
  2. stirringStir for 1 hour at -78° C.
  3. customquench with methanol (5 mL)
  4. additionpour into saturated ammonium chloride (100 mL)
  5. filtrationFilter
  6. customseparate the organic phase
  7. extractionextract the aqueous phase with ethyl acetate
  8. washwash with water and brine
  9. dry with materialDry (MgSO4)
  10. customevaporate the solvent in vacuo
  11. customPurify by chromatography (ethyl acetate)
  12. customrecrystallize (cyclohexane)

出典と根拠

ORDレコード
ord-1602ea0c7c6341799c4f3bf9d9dcc4b8
出典データセット
uspto-grants-1997_02
特許番号
US05602147

関連ノート

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