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

HRID 1681851ノート

反応式

HRID 1681851 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  1. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-d44808ae6391422abeb4ba581cbdf2e6
出典データセット
uspto-grants-1992_12
特許番号
US05175174

反応ノート

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