2-Aminopropanol → 2-(N-Hexadecanoyl)amino-1-propanol

HRID 34304

Reaction equation

HRID 34304 reaction equation
[CH3:1][CH:2]([NH2:5])[CH2:3][OH:4].[C:6](Cl)(=[O:22])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C(Cl)Cl>[C:6]([NH:5][CH:2]([CH3:1])[CH2:3][OH:4])(=[O:22])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 51262-AminopropanolHCID 8206Palmitoyl chloride

Product 1

HCID 184318022-(N-Hexadecanoyl)amino-1-propanolYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.00 g (53.2 mmol) of commercially obtained dl-2-amino-1-propanol b and 8.0 g (8.8 ml, 29.3 mmol) of hexadecanoyl chloride in 100 ml of CH2Cl2 was stirred at room temperature for hours. The solution was concentrated and the residue was boiled with 200 ml acetone and decanted. The solution was concentrated and the residue was chromatographed on silica gel using 50% ethylacetate in hexane to afford 4.15 g (51%) of the title compound as white needles, m.p. 75-76° C. Using the same procedure as in Example 19, the following compounds were prepared:

Workup

  1. concentrationThe solution was concentrated
  2. customdecanted
  3. concentrationThe solution was concentrated
  4. customthe residue was chromatographed on silica gel using 50% ethylacetate in hexane

Sources & evidence

ORD record
ord-9fed08b7a87d4dc89a917158d7429c2c
Source dataset
uspto-grants-1988_08
Patent number
US04761404

Linked notes

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