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

HRID 1681851Notes

Reaction equation

HRID 1681851 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d44808ae6391422abeb4ba581cbdf2e6
Source dataset
uspto-grants-1992_12
Patent number
US05175174

Reaction notes

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