1-Indanone → 1-(2-(Indan-1-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine

HRID 2396878Notes

Reaction equation

HRID 2396878 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:16][C:17]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=3)[CH2:21][CH2:20]2)=O)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1.C1(=O)C2C(=CC=CC=2)CC1.CP(OC(OC(CC)(CC)C)=O)(=O)[O-].COC1C=C(C2CCNCC2)C=CC=1OC>C1COCC1.[H][H].[Pd].O.CO>[CH:7]1([CH2:16][CH2:17][N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=3)[CH2:21][CH2:20]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1

Participants

10

Reactant 5

HCID 67351-IndanoneHCID 5458284-(3,4-Dimethoxyphenyl)piperidineHCID 189865361-(Indan-1-ylacetyl)-4-(3,4-dimethoxyphenyl)piperidineHCID 21226445Aluminium lithium hydride2×HCID 86749290Diethylethoxycarbonyl methanephosphonate

Product 1

HCID 189865301-(2-(Indan-1-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine

Reagents, catalysts & solvents 4

HCID 178506449HCID 178506449, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 0.6 g of lithium aluminium hydride in 35 ml of THF is treated dropwise with stirring under inert reaction conditions with a solution of 6.3 g of 1-(indan-1-ylacetyl)-4-(3,4-dimethoxyphenyl)piperidine [obtainable by reaction of 1-indanone with diethylethoxycarbonyl methanephosphonate, subsequent hydrogenation with H2 /Pd-C, conversion of the ester present to an acid chloride and amide formation with 4-(3,4-dimethoxyphenyl)piperidine] in 70 ml of THF and the mixture is boiled for 2 hours. A further 0.8 g of lithium aluminium hydride is then added and the mixture is refluxed for a further 3 hours. The reaction mixture is then treated with methanol and subsequently with water and worked up in the customary manner. Chromatography (methyl tertbutyl ether/petroleum ether/diethylamine) gives 1-(2-(indan-1-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine.

Workup

  1. additionis treated dropwise
  2. temperaturethe mixture is refluxed for a further 3 hours

Sources & evidence

ORD record
ord-ae271c8df8684344a584c5f1cdcb4833
Source dataset
uspto-grants-1996_02
Patent number
US05495022

Reaction notes

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