Sodium Hydroxide → HCID 19097467, compound

HRID 486075Notes

Reaction equation

HRID 486075 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH3:8])[C:4]([CH3:16])([CH2:9][CH2:10]C(OCC)=O)[CH:3]1[CH3:17].[N-:18]=[N+]=[N-].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH3:8])[C:4]([CH3:16])([CH2:9][CH2:10][NH2:18])[CH:3]1[CH3:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 19097402HCID 19097402, compound

Product 1

HCID 19097467HCID 19097467, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 1,2,3,4-tetramethyl-3-piperidinepropanoate (34.0 g, 141 mmol) was dissolved in concentrated sulfuric acid (300 mL) under a nitrogen atmosphere and the mixture was heated to 60° C. Sodium azide (18.35 g, 282 mmole) was then added in small portions (300-500 mg) over a three hour period at such a rate that a temperature range of 50°-70° C. was maintained. The mixture was then stirred at 60° C. for 2 hours, cooled to room temperature and poured onto ice-water (800 mL). The solution was basified with 35% NaOH and extracted with ether (3X). The organic layers were combined, dried over anhydrous MgSO4 and concentrated in vacuo to afford 18.5 g (71%) of 1,2,3,4-tetramethyl-3-piperidineethanamine as a yellow oil. The product was treated with ethereal HCl to afford the product as a dihydrochloride salt. The salt was isolated as a white powder and had a melting point of 233°-235° C.

Workup

  1. temperaturewas maintained
  2. temperaturecooled to room temperature
  3. additionpoured onto ice-water (800 mL)
  4. extractionextracted with ether (3X)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1470a9b9c59f4e48a6122086fa7a133f
Source dataset
uspto-grants-1994_03
Patent number
US05290796

Reaction notes

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