Ammonia → Ethyl (trans)-4-(aminomethyl)-3-ethoxy-1-piperidinecarboxylate

HRID 1264656Notes

Reaction equation

HRID 1264656 reaction equation
[C:1]([C@@H:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][C@H:4]1[O:14][CH2:15][CH3:16])#[N:2].N.[H][H]>CO.[Ni]>[NH2:2][CH2:1][C@@H:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][C@H:4]1[O:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 86589666Ethyl (trans)-4-cyano-3-ethoxy-1-piperidine-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86589667Ethyl (trans)-4-(aminomethyl)-3-ethoxy-1-piperidinecarboxylateYield 27.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate (13) (0.19 mol) in methanol saturated with NH3 (500 ml) was hydrogenated at 14° C. with Raney nickel as a catalyst. After uptake of hydrogen (2 equivalents), the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 95/5). The desired fractions were collected and the solvent was evaporated, yielding 12 g of ethyl (trans)-4-(aminomethyl)-3-ethoxy-1-piperidinecarboxylate (intermediate 14).

Workup

  1. customthe filtrate was evaporated
  2. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 95/5)
  3. customThe desired fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-069e9e9a191c43088bfea141962db08b
Source dataset
uspto-grants-2003_04
Patent number
US06544997B1

Reaction notes

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