Triethylamine → [Benzo[b]thiophene-2-yl][1-(2-phenylethyl)-4-piperidinyl]methanone

HRID 1450436

反応式

HRID 1450436 の反応式
C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([CH:21]([C:23]3[S:27][C:26]4[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=4[CH:24]=3)[OH:22])[CH2:17][CH2:16]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[S:27]1[C:23]([C:21]([CH:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:16][CH2:17]2)=[O:22])=[CH:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]1=2

参加物

6

反応物 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18930341alpha-[1-(2-Phenylethyl)-4-piperidinyl]-2-benzo[b]thiophenemethanol

生成物 1

HCID 18930331[Benzo[b]thiophene-2-yl][1-(2-phenylethyl)-4-piperidinyl]methanone

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

Dissolve oxalyl chloride (4.22 g, 33.28 mmol) in methylene chloride (200 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, dimethylsulfoxide (5.42 g, 69.33 mmol) and stir at -78° C. for 15 minutes. Add, by dropwise addition, a solution of α-[1-(2-phenylethyl)-4-piperidinyl]-2-benzo[b]thiophenemethanol in dimethylsulfoxide (150 mL). Stir at -78° C. for 30 minutes, add triethylamine (15.18 g, 0.150 mol) and stir at -78° C. for 1 hour. Remove the ice bath and stir for an additional 1.5 hours. Evaporate the solvent in vacuo and recrystallize (isopropanol) to give the title compound as a fluffy white crystalline solid; mp 129°-130° C.

後処理

  1. additionAdd, by dropwise addition
  2. stirringStir at -78° C. for 30 minutes
  3. stirringstir at -78° C. for 1 hour
  4. customRemove the ice bath
  5. stirringstir for an additional 1.5 hours
  6. customEvaporate the solvent in vacuo
  7. customrecrystallize (isopropanol)

出典と根拠

ORDレコード
ord-ab9e7411503545679f9b56bfd49fdf54
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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