1,3-Propanediamine → Gluconamide

HRID 2293652

Reaction equation

HRID 2293652 reaction equation
[C:1]1(=[O:12])[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[NH2:13]CCCN>CO>[O:12]=[C:1]([NH2:13])[C@@H:2]([C@H:4]([C@@H:6]([C@@H:8]([CH2:9][OH:10])[OH:11])[OH:7])[OH:5])[OH:3]

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 7027delta-Gluconolactone

Product 1

HCID 124042GluconamideYield 240.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A 100 ml round bottom flask equipped with a condenser, addition funnel, thermometer and mechanical stirrer was charged with D-glucono-1,5-lactone (5.4 g, 0.03 mole) and methanol (7 g). The suspension was heated to 40° C. over 15 minutes and the heating mantle removed. Soya-aminopropylamine (10.0 g, 0.03 mole) was added dropwise over 15 minutes with rapid stirring. The reaction mixture was cooled and placed in a refrigerator at 0° C. overnight. The white product was filtered, washed with cold isopropanol (3×100 ml) and dried under vacuum at 35° C. giving 14.1 g (92% yield) of soyaaminopropyl D-gluconamide with a melting point of 97°-100° C.

Workup

  1. customA 100 ml round bottom flask equipped with a condenser, addition funnel
  2. customthe heating mantle removed
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe white product was filtered
  5. washwashed with cold isopropanol (3×100 ml)
  6. customdried under vacuum at 35° C.

Sources & evidence

ORD record
ord-86d9fd50a6ec4140bdb6ac3f42177b07
Source dataset
uspto-grants-1997_11
Patent number
US05686603

Linked notes

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