Methanol → Ethyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

HRID 1789487Notes

Reaction equation

HRID 1789487 reaction equation
[OH:1][C:2]1([CH2:13][N+:14]([O-])=O)[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.CO.[H][H]>[Pd].C(O)(=O)C>[NH2:14][CH2:13][C:2]1([OH:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 887MethanolHCID 22708806Ethyl 4-hydroxy-4-(nitromethyl)-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 14049029Ethyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 73 parts of ethyl 4-hydroxy-4-(nitromethyl)-1-piperidinecarboxylate, 400 parts of methanol and 150 parts of acetic acid was hydrogenated in the Parr-apparatus 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. To the residue was added crushed ice and the whole was alkalized with potassium hydroxide. The aqueous phase was salted out with potassium carbonate and the product was extracted with benzene. The extract was dried, filtered and evaporated, yielding 63.5 parts of ethyl 4-(aminomethyl)-4-hydroxy-1-piperidinecarboxylate; mp. ±82° C. (intermediate 6).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionTo the residue was added
  4. customcrushed ice
  5. extractionthe product was extracted with benzene
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-446a94c66a0c4158844c2afd4599238d
Source dataset
uspto-grants-1987_08
Patent number
US04689330

Reaction notes

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