Hydrochloric Acid → 2-(4-Aminopiperidin-1-yl)ethan-1-ol

HRID 588049Notes

Reaction equation

HRID 588049 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10]C(=O)OC(C)(C)C)[CH2:6][CH2:5]1.Cl>C(O)C>[NH2:10][CH:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 45076484[1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 157334452-(4-Aminopiperidin-1-yl)ethan-1-olYield 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.58 g of tert-butyl 1-(2-hydroxyethyl)piperidin-4-ylcarbamate obtained in step 1 in 10 ml of ethanol was added 1 ml of conc. HCl, followed by stirring for 2 hrs under reflux. The reaction mixture was cooled to room temperature, and concentrated in a reduced pressure to remove solvent. The residue was added with 10 ml of distilled water, neutralized with saturated sodium hydrogen carbonate aqueous solution, and extracted twice with 10 ml of methylene chloride. After being dried over a desiccant, the fraction was concentrated in a reduced pressure to afford 0.33 g of the title compound (Yield: 95%). 1H NMR (CDCl3) δ 3.68 (s, 2H), 3.60 (t, 2H), 2.86 (d, 2H), 2.69 (m, 1H), 2.53 (t, 2H), 2.11 (t, 2H), 1.82 (d, 2H), 1.42 (t, 2H) ppm.

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated in a reduced pressure
  3. customto remove solvent
  4. additionThe residue was added with 10 ml of distilled water
  5. extractionextracted twice with 10 ml of methylene chloride
  6. customAfter being dried over a desiccant, the fraction
  7. concentrationwas concentrated in a reduced pressure

Sources & evidence

ORD record
ord-073a09ed8562437cbf4ede7277124b43
Source dataset
uspto-grants-2016_01
Patent number
US09227955B2

Reaction notes

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