Isopropylamine → Ethyl 4-[(propan-2-yl)amino]piperidine-1-carboxylate

HRID 1723419Notes

Reaction equation

HRID 1723419 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH3:13][CH:14]([NH2:16])[CH3:15].S1C=CC=C1.[H][H]>CO.[Pd]>[CH3:13][CH:14]([NH:16][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1)[CH3:15]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 8030ThiopheneHCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 15725096Ethyl 4-[(propan-2-yl)amino]piperidine-1-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 100 parts of ethyl 4-oxo-1-piperidinecarboxylate, 42 parts of 2-propanamine, 2 parts of a solution of thiophene in methanol 4% and 400 parts of methanol was hydrogenated at normal pressure and at room temperature with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 118 parts (94%) of ethyl 4-[(1-methylethyl)amino]-1-piperidinecarboxylate (1).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-fddf3c757ae2439da8781de9edd1e4e6
Source dataset
uspto-grants-1989_08
Patent number
US04861785

Reaction notes

Loading…