Sodium Chloride → {4-[(4-Butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)ethyl]amine

HRID 551894노트

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HRID 551894 반응식
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][NH2:30])=[CH:24][CH:23]=1.[BH4-].[Na+].[Na+].[Cl-]>C1(C)C=CC=CC=1.O>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH2:17][NH:30][CH2:29][CH2:28][C:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 674302-(4-Chlorophenyl)ethylamineHCID 4311764Sodium borohydrideHCID 113345124-[2-(4-Butylphenyl)ethynyl]benzaldehyde

생성물 1

HCID 57554507{4-[(4-Butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)ethyl]amine수율 73.6%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

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온도
0 °C

실험 절차

A solution of 4-[(4-butylphenyl)ethynyl]benzaldehyde (2.62 g, 10.0 mmol, intermediate to which may be obtained according to methods disclosed in EP03103780.7) and 2-(4-chlorophenyl)ethylamine (Aldrich, 1.56 g, 10 mmol) was heated at reflux in toluene (50 mL) for 12 hrs with azeotropic removal of water. The mixture was evaporated under vacuum and the residue was taken up in MeOH (60 mL) and chilled at 0° C. NaBH4(567 mg, 15.0 mmol) was added portionwise and the reaction mixture was stirred for 30 min at 0° C. and 3 hrs at rt. The reaction mixture was poured into a saturated solution of NaCl and extracted with Et2O. The combined organic layers were dried over MgSO4 and the solvents were removed under reduced pressure to give the crude product. Purification by chromatography on silicagel (EtOAc/c-hex 30/70) gave 2.96 g (54%) of the title compound as a white solid. HPLC, Rt: 5.0 min (purity: 99.9%).

후처리

  1. customThe mixture was evaporated under vacuum
  2. extractionextracted with Et2O
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customto give the crude product
  6. customPurification by chromatography on silicagel (EtOAc/c-hex 30/70)

출처 및 근거

ORD 기록
ord-45b22b9d1eb24b8c960859287ac9e5ce
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947851B2

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