Nitrogen → N-(3-amino-2-hydroxypropyl)-12-hydroxydodecanamide

HRID 1124

Reaction equation

HRID 1124 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][NH2:5].N#N.[OH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](OC)=[O:22]>C[O-].[Na+].C1COCC1>[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][NH:5][C:10](=[O:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22]

Participants

6

Reactant 3

HCID 947NitrogenHCID 611571,3-Diamino-2-propanolHCID 522424Methyl 12-hydroxydodecanoate

Product 1

HCID 19694634N-(3-amino-2-hydroxypropyl)-12-hydroxydodecanamideYield 75.7%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 100-ml two-necked flask equipped with a stirrer and dropping funnel was charged with 9.39 g (104 mmol) of 1,3-diamino-2-propanol and 0.047 g (0.87 mmol) of sodium methoxide. While heating and stirring the contents at 80° C. in an N2 atmosphere, a THF solution of 4.00 g (17.4 mmol) of methyl 12-hydroxydodecanate was added dropwise over 2.5 hours. Precipitate formed was washed with water and recrystallized from ethyl acetate-methanol (4:1 v/v), thereby obtaining 3.80 g (yield: 75%) of the title compound (IIh-12) as colorless powder.

Workup

  1. customA 100-ml two-necked flask equipped with a stirrer
  2. temperatureWhile heating
  3. customPrecipitate formed
  4. washwas washed with water
  5. customrecrystallized from ethyl acetate-methanol (4:1 v/v)

Sources & evidence

ORD record
ord-c24607cade224f55921e8fa774f3f6f4
Source dataset
uspto-grants-1998_03
Patent number
US05723497

Linked notes

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