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

HRID 2063723노트

반응식

HRID 2063723 반응식
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]

참가 물질

5

반응물 2

HCID 313Hydrochloric Acid2회HCID 66887575{1-Butyl-4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexyl}dimethylamine

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eb49fdee4bb74f9aa968ba8620a289c6
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288406B2

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