1-Phenylpiperazine → 1-(3-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propyl)-4-phenylpiperazine

HRID 386990노트

반응식

HRID 386990 반응식
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:16][CH2:17][CH:18]=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:20]1([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CCCCCC.CCOC(C)=O.O>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:16][CH2:17][CH2:18][N:29]2[CH2:30][CH2:31][N:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:27][CH2:28]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

9

반응물 4

HCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866399163-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propanal

생성물 1

HCID 250646411-(3-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propyl)-4-phenylpiperazine

시약·촉매·용매 4

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

3-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propanal (80 mg, 312 mmol) and 1-phenylpiperazine (0.047 mL, 0.312 mmol) were dissolved in 5 mL of CH2Cl2, and then 0.7 g of 4 molecular sieve powder was added thereto and stirred. Diisopropylethylamine (DIPEA; 54 mL, 0.312 mmol) was slowly added thereto, and stirred for 30 min at room temperature. Then, NaBH(OAc)3 (231 mg, 1.092 mmol) was added thereto and stirred for 12 hours at room temperature. The reaction progress and completion were confirmed by TLC. Upon completion of the reaction, water (0.1 mL) was added to the reaction mixture and then stirred for 3 min. 81 mg (64%) of target compound was obtained via column chromatography (EtOAc:Hexane=4:1, v/v).

후처리

  1. stirringstirred for 30 min at room temperature
  2. stirringstirred for 12 hours at room temperature
  3. additionwas added to the reaction mixture
  4. stirringstirred for 3 min

출처 및 근거

ORD 기록
ord-05039d42d05242a8b9e2daabd24721ad
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372844B2

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