Acetic Acid → 4-(N-Boc-amino)piperidine

HRID 745840Notes

Reaction equation

HRID 745840 reaction equation
CC([N:5]([CH:9]1[CH2:14][CH2:13][N:12](CC2C=CC=CC=2)[CH2:11][CH2:10]1)[C:6](=[O:8])[O-:7])(C)C.C(O)(=O)C.[CH3:26][C:27](N(C1CCNCC1)C(=O)[O-])([CH3:29])[CH3:28]>[Pd].C(O)C>[NH:12]1[CH2:11][CH2:10][CH:9]([NH:5][C:6](=[O:8])[O:7][C:27]([CH3:29])([CH3:28])[CH3:26])[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 57446144HCID 57446144, compoundHCID 86740909HCID 86740909, compound

Product 1

HCID 7238334-(N-Boc-amino)piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1,1-dimethylethyl[1-(phenylmethyl)-4-piperidinyl]carbamate (0.355 mole), 10% palladium-on-carbon (10.0 g.) in 43 ml. of acetic acid and 90 ml. of ethanol was hydrogenated under low pressure at room temperature for a 96 hr. period. The reaction mixture was filtered and concentrated in vacuo. Residual oil was taken up in chloroform, washed with 20% aqueous sodium carbonate solution and the aqueous phase extracted with additional chloroform. The combined chloroform extracts were dried (MgSO4) and evaporated in vacuo to afford 64.2 g. (90%) of 1,1-dimethylethyl4-piperidinylcarbamate, m.p. 153°-157°.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. washwashed with 20% aqueous sodium carbonate solution
  4. extractionthe aqueous phase extracted with additional chloroform
  5. dry with materialThe combined chloroform extracts were dried (MgSO4)
  6. customevaporated in vacuo
  7. customto afford 64.2 g

Sources & evidence

ORD record
ord-b9d1c32247b04d888b44f7957caeae1e
Source dataset
uspto-grants-1986_07
Patent number
US04600758

Reaction notes

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