2,3-dihydroquinolin-4(1H)-one → 1-(2-(1,2,3,4-Tetrahydroquinolin-4-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine

HRID 2396884Notes

Reaction equation

HRID 2396884 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=3)[CH2:16][CH2:15]2)=O)[CH2:3][CH2:2]1.N1C2C(=CC=CC=2)C(=O)CC1.CP(OC(OC(CC)(CC)C)=O)(=O)[O-].COC1C=C(C2CCNCC2)C=CC=1OC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>[H][H].[Pd]>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][CH2:12][N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=3)[CH2:16][CH2:15]2)[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 1171582,3-dihydroquinolin-4(1H)-oneHCID 5458284-(3,4-Dimethoxyphenyl)piperidineHCID 189865431-(1,2,3,4-Tetrahydroquinolin-4-yl-acetyl)-4-(3,4-dimethoxyphenyl)piperidineHCID 21226445Aluminium lithium hydrideHCID 86749290Diethylethoxycarbonyl methanephosphonate

Product 1

HCID 98428631-(2-(1,2,3,4-Tetrahydroquinolin-4-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine

Reagents, catalysts & solvents 1

HCID 178506449HCID 178506449, compoundCatalyst

Procedure

Analogously to Example 2, reduction of 1-(1,2,3,4-tetrahydroquinolin-4-yl-acetyl)-4-(3,4-dimethoxyphenyl)piperidine [obtainable by reaction of 1,2,3,4-tetrahydroquinolin-4-one with diethylethoxycarbonyl methanephosphonate, subsequent hydrogenation with H2 /Pd-C, hydrolysis of the ester present and subsequent amide formation with 4-(3,4-dimethoxyphenyl)piperidine] using lithium aluminium hydride gives 1-(2-(1,2,3,4-tetrahydroquinolin-4-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine, m.p. 235°-236° (dihydrochloride).

Sources & evidence

ORD record
ord-ed4875e7ec314d96aca57b39afd46e81
Source dataset
uspto-grants-1996_02
Patent number
US05495022

Reaction notes

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