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 975819ノート

反応式

HRID 975819 の反応式
[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

参加物

9

反応物 6

HCID 313Hydrochloric Acid2 回HCID 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

生成物 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-one収率 47%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-6d14e0d9ea4149c8a12970353c0a690a
出典データセット
uspto-grants-1997_03
特許番号
US05610154

反応ノート

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