1-Chloro-4-(trifluoromethyl)benzene → 1-[4-(Trifluoromethyl)phenyl]piperidine

HRID 1884174

반응식

HRID 1884174 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:12]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

참가 물질

6

반응물 3

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 8082PiperidineHCID 23676156Sodium t-butoxide

생성물 1

HCID 4250921-[4-(Trifluoromethyl)phenyl]piperidine수율 23.4%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

The general procedure from Example 1A was followed using 4-chloro-benzotrifluoride (650 mg, 3.6 mmol) and piperidine (258 mg, 3.0 mmol) with Pd2(dba)3 (55 mg, 0.081 mmol) and (Me3C)2PH(O) (21.0 mg, 0.126 mmol) and NaOtBu (432 mg, 4.5 mmol) in 6.0 mL of toluene. After 48 h, the reaction mixture was chromatographed with 5% ethyl acetate/hexane to give 161 mg (23% yield) of 4-piperidinobenzotrifluoride. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ7.36 (d, J=8.78 Hz, 2H), 6.82 (d, J=8.79 Hz, 2H), 3.18 (m, 4H), 1.60 (m, 4H), 1.54 (m, 2H) ppm. 13C NMR (125 MHz, CDCl3): d 153.7, 127.6, 126.3, 114.5, 49.2, 25.4, 24.2 ppm. MS: Calculated for C12H14F3N(M+): 229.1. Found: 230.2 (M++H).

후처리

  1. customthe reaction mixture was chromatographed with 5% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-43cda23275ca41288a9ae06a1e239ee4
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06762330B2

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