Potassium Carbonate → N-[5-[4-(diphenylmethoxy)piperidino]pentyl]phthalimide

HRID 1169124ノート

反応式

HRID 1169124 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17].[C:18]1([CH:24]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:32]1([CH:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]3[C:11](=[O:12])[C:10]4=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]4[C:8]3=[O:17])[CH2:28][CH2:27]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 136770N-(5-Bromopentyl)phthalimideHCID 30175844-Benzhydryloxypiperidine

生成物 1

HCID 22989373N-[5-[4-(diphenylmethoxy)piperidino]pentyl]phthalimide収率 87.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3.70 g of potassium phthalimide was dissolved in 20 ml of N,N-dimethylformamide; 5.4 ml of 1,5-dibromopentane was added, followed by stirring at room temperature for 15 hours. Ice water was added to the reaction mixture, followed by extraction with ethyl acetate; the extract was washed with saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (4:1). The desired fraction was collected to yield 4.68 g of N-(5-bromopentyl)phthalimide as an oily substance. 4.68 g of N-(5-bromopentyl)phthalimide and 4.25 g of 4-(diphenylmethoxy)piperidine were dissolved in 30 ml of N,N-dimethylformamide; 2.42 g of potassium carbonate was added, followed by stirring at room temperature for 15 hours. Ice water was added to the reaction mixture, followed by extraction with ethyl acetate; the extract was washed with saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate-triethylamine (50:50:1). The desired fraction was collected to yield 6.67 g of N-[5-[4-(diphenylmethoxy)piperidino]pentyl]phthalimide as an oily substance. 6.6 g of N-[5-[4-(diphenylmethoxy)piperidino]pentyl]phthalimide was dissolved in 30 ml of ethanol; 0.694 ml of hydrazine monohydrate was added, followed by thermal refluxing for 3 hours. After cooling, the mixture was concentrated under reduced pressure; ethyl acetate was added to the residue; the crystal precipitated was collected, dissolved in 15 ml of a 1N aqueous solution of sodium hydroxide and 20 ml of water and extracted with ethyl acetate; the extract was washed with saline, dried over sodium sulfate and concentrated under reduced pressure; the crystal obtained was collected to yield 3.29 g of the title compound.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe extract was washed with saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with hexane-ethyl acetate-triethylamine (50:50:1)
  6. customThe desired fraction was collected

出典と根拠

ORDレコード
ord-6d798862efea43ff94043fb9190767a5
出典データセット
uspto-grants-2003_09
特許番号
US06627630B1

反応ノート

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