tert-Butyl 4-oxopiperidine-1-carboxylate → tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

HRID 1986041Notes

Reaction equation

HRID 1986041 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15]([NH2:17])[CH3:16].O>C(O)C.[Pt]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:16][CH2:15][NH2:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 86622996HCID 86622996, compound

Product 1

HCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylateYield 107%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

1-tert-Butoxycarbonyl-4-piperidone (15 g, 75.28 mmol) was dissolved in ethanol (150 ml) and treated with 70% ethylamine/H2O (6.06 ml, 75.29 mmol), followed by 5% Pt/C JM type 117 (2.25 g, 20 wt %). The reaction mixture was subjected to hydrogenation at 2 bar, 50° C. with stiring for 4 hours. The reaction mixture was purged with nitrogen and filtered through GF/F filter paper. The catalyst was washed with ethanol (2×15 ml). The liquors were combined and evaporated to dryness to give N-(1-tert-butoxycarbonyl-4-piperidinyl)ethylamine as a colourless oil (18.33 g, 107%).

Workup

  1. customwas subjected to hydrogenation at 2 bar, 50° C.
  2. customThe reaction mixture was purged with nitrogen
  3. filtrationfiltered through GF/F
  4. filtrationfilter paper
  5. washThe catalyst was washed with ethanol (2×15 ml)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-74ac9a45553e4d83a87f03ed20357fae
Source dataset
uspto-grants-2009_06
Patent number
US07547789B2

Reaction notes

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