Hydrochloric Acid → 1-(4-Butyl-4-dimethylaminocyclohexyl)-2-phenylethanol

HRID 2063723ノート

反応式

HRID 2063723 の反応式
Cl.[CH2:2]([C:6]1([N:26]([CH3:28])[CH3:27])[CH2:11][CH2:10][CH:9]([CH:12]([O:20]C(OCC)C)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5]>O1CCCC1.C(Cl)Cl>[CH2:2]([C:6]1([N:26]([CH3:27])[CH3:28])[CH2:11][CH2:10][CH:9]([CH:12]([OH:20])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5]

参加物

5

反応物 2

HCID 313Hydrochloric Acid2 回HCID 66887575{1-Butyl-4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexyl}dimethylamine

生成物 1

HCID 442521081-(4-Butyl-4-dimethylaminocyclohexyl)-2-phenylethanol

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2 M hydrochloric acid (20 ml) was added to a solution of {1-butyl-4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexyl}dimethylamine (1.09 g, 2.90 mmol) in anhydrous tetrahydrofuran (20 ml) and the mixture was stirred at room temperature for 3 d. The tetrahydrofuran was removed i. vac. and the acid aqueous solution was extracted with diethyl ether (3×10 ml) and thereafter rendered alkaline with 4 M sodium hydroxide solution. The alkaline phase was extracted with methylene chloride (4×10 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac. The crude product (646 mg) was purified by flash chromatography with methylene chloride/methanol (9:1→8:2→0:1). The product obtained in this way was in the form of the hydrochloride. It was taken up in methylene chloride and the suspension was washed with saturated potassium carbonate solution. The organic phase was dried with sodium sulfate and concentrated i. vac.

後処理

  1. customThe tetrahydrofuran was removed i
  2. extractionand the acid aqueous solution was extracted with diethyl ether (3×10 ml)
  3. extractionThe alkaline phase was extracted with methylene chloride (4×10 ml)
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. concentrationconcentrated i
  6. customThe crude product (646 mg) was purified by flash chromatography with methylene chloride/methanol (9:1→8:2→0:1)
  7. customThe product obtained in this way
  8. washthe suspension was washed with saturated potassium carbonate solution
  9. dry with materialThe organic phase was dried with sodium sulfate
  10. concentrationconcentrated i

出典と根拠

ORDレコード
ord-eb49fdee4bb74f9aa968ba8620a289c6
出典データセット
uspto-grants-2012_10
特許番号
US08288406B2

反応ノート

読み込み中…