Dodecanoyl chloride → HCID 23371135, compound

HRID 1899746Notes

Reaction equation

HRID 1899746 reaction equation
[C:1](Cl)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][OH:27])[CH2:21][CH2:20]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[OH:27][CH2:26][CH2:25][N:22]1[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][CH2:16][NH:15][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 2552832-[4-(3-Aminopropyl)piperazin-1-yl]ethan-1-olHCID 516892Sodium Bicarbonate

Product 1

HCID 23371135HCID 23371135, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 50 mL chloroform solution of 2.45 g. (0.0112 mol) of dodecanoyl chloride was added dropwise under argon to an ice cold 50 mL chloroform solution of 2.12 g. (0.0113 mol) of N-(3-aminopropyl)-N'-(2-hydroxyethyl) piperazine and stirred for one hour maintaining the temperature between 2°-4° C. This reaction mixture was then treated with 100 mL of aqueous sodium bicarbonate and extracted with chloroform (2×50 mL). The combined chloroform layers were washed with aqueous sodium bicarbonate (2×50 mL), dried (MgSO4), filtered, and concentrated in vacuo. The remaining solid was crystallized in ethyl acetate/hexane to yield 1.69 g. (40.8%)of the subject product.

Workup

  1. temperaturemaintaining the temperature between 2°-4° C
  2. extractionextracted with chloroform (2×50 mL)
  3. washThe combined chloroform layers were washed with aqueous sodium bicarbonate (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe remaining solid was crystallized in ethyl acetate/hexane
  8. customto yield 1.69 g

Sources & evidence

ORD record
ord-fe54a2205d69463793424f3fd2a70176
Source dataset
uspto-grants-1996_11
Patent number
US05573726

Reaction notes

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