Triethylamine → HCID 178418330, 화합물

HRID 1737933

반응식

HRID 1737933 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.CN(C1C=CC=CN=1)C.[Cl:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1.[OH-].[Na+]>C(Cl)Cl.O>[Cl:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([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:40])=[CH:37][CH:36]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 14798Sodium HydroxideHCID 218852-DimethylaminopyridineHCID 178418380HCID 178418380, 화합물

생성물 1

HCID 178418330HCID 178418330, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

0.24 g (0.001 mol) of cis-4-(4-dimethylaminomethylphenyl)-cyclohexanol, 0.34 ml (0.0025 mol) of triethylamine and 0.12 g (0.001 mol) of dimethylaminopyridine are dissolved in 20 ml of methylene chloride, mixed with 0.175 g (0.001 mol) of 4-chlorobenzoylchloride and stirred for 12 hours at ambient temperature. The reaction mixture is combined with water and adjusted to pH 12-13 using sodium hydroxide solution. The methylene chloride phase is separated off, the aqueous phase is extracted several times with methylene chloride and the combined organic phases are washed with saturated saline solution, dried and evaporated down in vacuo. The residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=45:1) White crystals. Melting point: 96-97° C. Yield: 0.27 g (73% of theory)

후처리

  1. customThe methylene chloride phase is separated off
  2. extractionthe aqueous phase is extracted several times with methylene chloride
  3. washthe combined organic phases are washed with saturated saline solution
  4. customdried
  5. customevaporated down in vacuo
  6. customThe residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=45:1) White crystals

출처 및 근거

ORD 기록
ord-e767f0709d4045e28d85c33d5f9210fc
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962507

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