Formic Acid → 4-(N,N-diethylamino)-1-(4-nitrophenyl)-1,2,3,6-tetrahydropyridine

HRID 1681851노트

반응식

HRID 1681851 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18].C(O)=O>C1(C)C=CC=CC=1>[CH2:17]([N:19]([C:13]1[CH2:12][CH2:11][N:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:15][CH:14]=1)[CH2:20][CH3:21])[CH3:18]

참가 물질

5

반응물 3

HCID 284Formic AcidHCID 8021DiethylamineHCID 38425621-(4-Nitrophenyl)piperidin-4-one

생성물 1

HCID 198043464-(N,N-diethylamino)-1-(4-nitrophenyl)-1,2,3,6-tetrahydropyridine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

5.0 g (22.7 mmol) of 1-(4-nitrophenyl)-4-piperidone, 16.0 g (220 mmol) of diethylamine and 5 ml of formic acid in 150 ml of toluene were refluxed with a water trap for 5 h. The solvent was removed under reduced pressure, and 4-(N,N-diethylamino)-1-(4-nitrophenyl)-1,2,3,6-tetrahydropyridine was obtained as crude product. 3.45 g (92.5 mmol) of sodium borohydride were added a little at a time to this crude product in 150 ml of ethanol at 10° C. The mixture was left to stir at room temperature for 3 h and then the solvent was removed under reduced pressure. The residue was partitioned between water and methylene chloride, and the organic phase was dried and concentrated under reduced pressure. This crude product was dissolved in a little isopropanol, and ethereal hydrogen chloride solution was added to give 5.5 g of 4-(N,N-diethylamino)-1-(4-nitrophenyl)piperidine hydrochloride, which was identical to the product from preparation 1. Melting point 183°- 184° C.

후처리

  1. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-d44808ae6391422abeb4ba581cbdf2e6
출처 데이터셋
uspto-grants-1992_12
특허 번호
US05175174

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