Sodium Carbonate → HCID 86682891, compound

HRID 1522853Notes

Reaction equation

HRID 1522853 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-bb5c8ec6087e46b0be41d6fca6bf4fae
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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