Potassium Carbonate → N-benzyl-1-hydroxy-ethylamine

HRID 1645242Notes

Reaction equation

HRID 1645242 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9]CC(O)=O.C([O-])([O-])=O.[K+].[K+].[C:20]([O:24]C(OC(OC(C)(C)C)=O)=O)(C)(C)[CH3:21]>C(OC(=O)C)C.O.O1CCOCC1>[CH2:7]([NH:2][CH:20]([OH:24])[CH3:21])[C:6]1[CH:5]=[CH:4][CH:3]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 124163274-(Piperidin-2-yl)butanoic acid--hydrogen chloride (1/1)

Product 1

HCID 18470673N-benzyl-1-hydroxy-ethylamineYield 179.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Piperidin-2-ylbutanoic acid Hydrochloride (10.0 g, 48.3 mmol), and K2CO3 (26.6 g, 193.1 mmol) was dissolved in dest. water (70 ml) and Dioxane (124 ml). The reaction mixture was cooled to 0° C. and at this temperature Di-tert-butyldicarbonate (11.4 g, 53.1 mmol) was added slowly. The reaction mixture was stirred for 24 h at room temperature. After completion of the reaction water and Ethylacetate were added, the two phases were separated. The aqueous Phase was extracted once with Ethylacetate. Afterwards the aqueous Phase was triturated with 2 M HCL (aqueous) to reach pH=2. At this pH the aqueous phase was extracted 4× with Dichloromethane. The combined organic layers were dried over Magnesium sulfate, filtered out and evaporated to complete dryness to give (2) (13.13 g, 100%).

Workup

  1. additionwas added slowly
  2. additionwere added
  3. customthe two phases were separated
  4. extractionThe aqueous Phase was extracted once with Ethylacetate
  5. customAfterwards the aqueous Phase was triturated with 2 M HCL (aqueous)
  6. extractionAt this pH the aqueous phase was extracted 4× with Dichloromethane
  7. dry with materialThe combined organic layers were dried over Magnesium sulfate
  8. filtrationfiltered out
  9. customevaporated

Sources & evidence

ORD record
ord-ee14a51cc494414b9b203085a9257dd7
Source dataset
uspto-grants-2012_02
Patent number
US08124624B2

Reaction notes

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