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3-(Trifluoromethyl)aniline → 1-Boc-4-(3-trifluoromethyl-phenylamino)-piperidine

HRID 43348
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HRID 43348 반응식
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[F:15][C:16]([F:24])([F:25])[C:17]1[CH:18]=[C:19]([NH:20][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH:21]=[CH:22][CH:23]=1
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참가 물질

6

반응물 4

HCID 73753-(Trifluoromethyl)anilineHCID 516892Sodium BicarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 37223301-Boc-4-(3-trifluoromethyl-phenylamino)-piperidine수율 99.9%

시약·촉매·용매 1

HCID 11
1,2-Dichloroethane
용매

실험 절차

A Solution of 1,1-Dimethylethyl 4-Oxo-1-Piperidinecarboxylate (0.5 g, 2.5 mmol), 3-(trifluoromethyl)aniline (0.402 g, 2.5 mmol) and sodium tri(acetoxy)borohydride (0.80 g, 3.75 mmol) in 1,2-DCE (5 ml) was stirred at room temperature, under argon overnight. Saturated aq. NaHCO3 solution (15 ml) was added and stirring continued for 1 h. The reaction mixture was extracted with DCM and the organic phase concentrated in vacuo. Recrystallisation of the solid residue gave the title compound as a white solid (0.86 g). δH (CDCl3, 250 MHz)) 7.25 (1H, t), 6.92 (1H, d), 6.75 (2H, m), 4.06 (2H, m), 3.45 (1H, m), 2.94 (2H, m), 2.04 (2H, m), 1.46 (9H, s), 1.36 (2H, m).

후처리

  1. extractionThe reaction mixture was extracted with DCM
  2. concentrationthe organic phase concentrated in vacuo
  3. customRecrystallisation of the solid residue

출처 및 근거

ORD 기록
ord-0341eb119a7e42ef945e757759224d7c
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08536182B2

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