Hydrochloric Acid → 4-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-2-phenyl-1(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-butan-1-one

HRID 975819노트

반응식

HRID 975819 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](O)=[O:19])[CH2:11][CH2:10]1.[CH3:27][C:28]12[CH2:35][CH:32]([NH:33][CH2:34]1)[CH2:31][C:30]([CH3:37])([CH3:36])[CH2:29]2.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[OH-].[Na+].Cl>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([N:33]2[CH2:34][C:28]3([CH3:27])[CH2:35][CH:32]2[CH2:31][C:30]([CH3:37])([CH3:36])[CH2:29]3)=[O:19])[CH2:13][CH2:14]1

참가 물질

9

반응물 6

HCID 313Hydrochloric Acid2회HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 1037871,3,3-Trimethyl-6-azabicyclo(3.2.1)octaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 98634284-[4-(2-Methoxyphenyl)piperazin-1-yl]-2-phenylbutanoic acid

생성물 1

HCID 199683574-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-2-phenyl-1(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-butan-1-one수율 47%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-[4-(2-methoxyphenyl) piperazin-1-yl]-2-phenylbutanoic acid (1.70 g, 5.0 mmole), 1,3,3-trimethyl-6-azabicyclo[3.2.1]-octane (0.77 g, 5.0 mmole), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.96 g, 5.0 mmole) and triethylamine (0.55 g, 5.0 mmole) in methylene chloride (10 mL) was stirred at ambient temperature for 48 hr. The mixture was poured into 1N sodium hydroxide (75 mL) and extracted with ethyl acetate (3×75 mL). The combined ethyl acetate layer was washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to give crude product. This material was treated with 1.1 equivalent of 1N hydrogen chloride in ether (100 mL) to give 1.15 g of the title compound as the hydrochloride sequihydrate, m.p. 110°-145° C. (dec.).

후처리

  1. extractionextracted with ethyl acetate (3×75 mL)
  2. washThe combined ethyl acetate layer was washed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give crude product

출처 및 근거

ORD 기록
ord-6d14e0d9ea4149c8a12970353c0a690a
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05610154

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