Diisopropylethylamine → HCID 178487196、化合物

HRID 1762584ノート

反応式

HRID 1762584 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:9]=[C:8]([CH2:10]OS(C)(=O)=O)[C:7]=2[CH:16]=1.[OH2:17].Cl.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1=O.C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:9]=[C:8]([CH2:10][N:19]3[CH2:24][CH2:23][C:22](=[O:17])[CH2:21][CH2:20]3)[C:7]=2[CH:16]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 22021827Piperidone monohydrate hydrochlorideHCID 178487221HCID 178487221、化合物

生成物 1

HCID 178487196HCID 178487196、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 12.11 g (50 mmol) of methanesulphonic acid (5-methoxybenzocyclobuten-1-ylmethyl) ester in 100 ml of dimethylformamide there are added first 8.45 g (55 mmol) of piperidone hydrochloride monohydrate and then 22.62 g (175 mmol) of N-ethyl-N,N-diisopropylamine. The mixture is stirred at 80° C. for 18 hours and, after cooling, is concentrated to dryness by evaporation under reduced pressure. The residue is dissolved in diethyl ether and washed with water. The organic phase is separated off and extracted with 2N hydrochloric acid. The hydrochloric acid extracts are combined, rendered alkaline at reduced temperature with sodium hydroxide solution and extracted with dichloromethane. The extracts are combined, dried over sodium sulphate and concentrated to dryness by evaporation under reduced pressure. A dark brown resin is obtained which is purified by chromatography on 350 g of silica gel (0.040-0.063 mm) with toluene/ethyl acetate (1:1). 1-[(5-methoxybenzocyclobuten-1-yl)methyl]piperidin-4-one is obtained in the form of a light-yellow oil.

後処理

  1. temperatureafter cooling
  2. concentrationis concentrated to dryness by evaporation under reduced pressure
  3. dissolutionThe residue is dissolved in diethyl ether
  4. washwashed with water
  5. customThe organic phase is separated off
  6. extractionextracted with 2N hydrochloric acid
  7. extractionextracted with dichloromethane
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated to dryness by evaporation under reduced pressure
  10. customA dark brown resin is obtained which
  11. customis purified by chromatography on 350 g of silica gel (0.040-0.063 mm) with toluene/ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-cb9edf5a488d4e68926d25e35618d88b
出典データセット
uspto-grants-1989_05
特許番号
US04833169

反応ノート

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