Diisopropyl Ether → Benzyl 4-(2-oxoethyl)piperidine-1-carboxylate

HRID 1195662Notes

Reaction equation

HRID 1195662 reaction equation
Cl[C:2](=[O:20])[CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1.S1C=CC=C1.O(C(C)C)C(C)C.[H][H]>[Pd].CN(C)C(=O)C>[O:20]=[CH:2][CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 8030ThiopheneHCID 20479781Phenylmethyl 4-(2-chloro-2-oxoethyl)-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 22278282Benzyl 4-(2-oxoethyl)piperidine-1-carboxylateYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 90 parts of (phenylmethyl) 4-(2- chloro-2-oxoethyl)-1-piperidinecarboxylate, 90 parts of N,N-dimethylacetamide 6 parts of a thiophene solution and 438 parts of 2,2'-oxybispropane was hydrogenated at normal pressure and at room temperature in the presence of 5 parts of palladium-on-charcoal 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was taken up in water. The separated organic layer was dried, filtered and evaporated, yielding 75 parts (95.7%) of (phenylmethyl) 4-(2-oxoethyl)-1-piperidinecarboxylate as a residue (interm. 7).

Workup

  1. filtrationthe catalyst was filtered off
  2. customThe separated organic layer was dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f0109f1715e245e9a194756130010a09
Source dataset
uspto-grants-1992_05
Patent number
US05112825

Reaction notes

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