Triethylamine → HCID 178418352, 화합물

HRID 1651

반응식

HRID 1651 반응식
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH3:3].C(N(CC)CC)C.[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1.[OH-].[Na+]>C(Cl)Cl.O>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([O:17][C@H:14]2[CH2:15][CH2:16][C@H:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[CH:6][CH:7]=3)[CH2:12][CH2:13]2)=[O:31])=[CH:28][CH:27]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 14798Sodium HydroxideHCID 178418401HCID 178418401, 화합물

생성물 1

HCID 178418352HCID 178418352, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of 1.0 g (0.0043 mol) of trans-4-(4-dimethylaminomethylphenyl)-cyclohexanol and 0.6 ml of triethylamine in 50 ml of methylene chloride is combined, dropwise, with 0.75 g (0.0043 mol) of 4-chlorobenzoylchloride, with stirring, and refluxed for 3 hours. After cooling, 50 ml of water are added, the mixture is adjusted to pH 12-13 with sodium hydroxide solution, the methylene chloride phase is separated off and the aqueous phase is extracted once more with methylene chloride. The combined organic phases are dried over sodium sulphate and evaporated down in vacuo. The solid residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=40:1). White crystals are obtained with a melting point of 94°-95° C.

후처리

  1. temperaturerefluxed for 3 hours
  2. temperatureAfter cooling
  3. customthe methylene chloride phase is separated off
  4. extractionthe aqueous phase is extracted once more with methylene chloride
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. customevaporated down in vacuo
  7. customThe solid residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=40:1)
  8. customWhite crystals are obtained with a melting point of 94°-95° C.

출처 및 근거

ORD 기록
ord-fe8da988a6f64ed0968009c91353edde
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726205

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