Benzene, (2-bromoethoxy)- → ethyl N-(2-phenoxyethyl)piperidine-3-carboxylate

HRID 962464

反応式

HRID 962464 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.[C:12]1([O:18][CH2:19][CH2:20]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>>[O:18]([CH2:19][CH2:20][N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

4

反応物 3

HCID 68526Benzene, (2-bromoethoxy)-HCID 98969Ethyl nipecotateHCID 516892Sodium Bicarbonate

生成物 1

HCID 19085394ethyl N-(2-phenoxyethyl)piperidine-3-carboxylate

実験手順

A mixture of ethyl 3-piperidinecarboxylate (20.58 g), 2-bromoethyl phenyl ether (26.31 g), sodium bicarbonate (10.99 g) and IMS (100 ml) was boiled under reflux for 16 hours. The mixture was evaporated to dryness then diluted with water (100 ml) and 2M sodium hydroxide solution (20 ml). This mixture was extracted with dichloromethane and the combined dichloromethane extracts were extracted with 2M hydrochloric acid. The acidic extracts were washed with dichloromethane and then basified with 2M sodium hydroxide solution. This mixture was extracted with dichloromethane to give ethyl N-(2-phenoxyethyl)piperidine-3-carboxylate as an oil. A sample of the oil was dissolved in ether and ethereal oxalic acid was added. The precipitate was filtered off and recrystallised from aqueous propan-2-ol to give ethyl N-(2-phenoxyethyl)piperidine-3-carboxylate oxalate hemihydrate, m.p. 131°-132° C.

後処理

  1. temperatureunder reflux for 16 hours
  2. customThe mixture was evaporated to dryness
  3. additionthen diluted with water (100 ml) and 2M sodium hydroxide solution (20 ml)
  4. extractionThis mixture was extracted with dichloromethane
  5. extractionthe combined dichloromethane extracts were extracted with 2M hydrochloric acid
  6. washThe acidic extracts were washed with dichloromethane
  7. extractionThis mixture was extracted with dichloromethane

出典と根拠

ORDレコード
ord-62e837d0dcf245299b0b9b6410c44e02
出典データセット
uspto-grants-1998_06
特許番号
US05760035

関連ノート

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