Sodium Carbonate → HCID 86682891, compound

HRID 2368899Notes

Reaction equation

HRID 2368899 reaction equation
[NH2:1][C@@H:2]([CH3:5])[CH2:3][OH:4].I[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]I.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C>[N:1]1([C@@H:2]([CH3:5])[CH2:3][OH:4])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123541,5-DiiodopentaneHCID 80307L-Alaninol

Product 1

HCID 86682891HCID 86682891, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of (S)-2-aminopropan-1-ol (2.0 mL, 26 mmol), 1,5-diiodopentane (4.7 mL), and sodium carbonate (7.13 g, 67.3 mmol) in i-propanol (200 mL) was heated at reflux overnight. The reaction mixture was concentrated, diluted with ethyl acetate (100 mL) and the insoluble solid was filtered off. The solvent was removed under reduced pressure and the residue was purified on a silica gel column to yield ((S)-2-(piperidin-1-yl)propan-1-ol (2.0 g, 54%) as a clear oil. 1H NMR (CDCl3): δ 3.37 (dd, 1H), 3.30 (t, 1H), 2.78 (m, 1H), 2.62 (m, 2H), 2.33 (m, 2H), 1.40-1.70 (m, 6H), 0.86 (d, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with ethyl acetate (100 mL)
  5. filtrationthe insoluble solid was filtered off
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-ea2cccc5d8df45a696f261a120666e08
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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