Hexamethylenediamine → Butyl ethyl(3-aminopropyl)phosphinate

HRID 576015Notes

Reaction equation

HRID 576015 reaction equation
NCCCCCCN.[CH2:9]([P:11]([CH2:18][CH2:19][C:20]#[N:21])(=[O:17])[O:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:10].[H][H]>[Ni].[OH-].[K+].O>[CH2:9]([P:11]([CH2:18][CH2:19][CH2:20][NH2:21])(=[O:17])[O:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:10]

Participants

7

Reactant 3

HCID 16402HexamethylenediamineHCID 19606949Butyl ethyl(2-cyanoethyl)phosphinateHCID 178418361HCID 178418361, compound

Product 1

HCID 46212699Butyl ethyl(3-aminopropyl)phosphinateYield 81%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 14797Potassium HydroxideCatalystHCID 962WaterSolvent

Procedure

In a glass autoclave, 240 g of hexamethylenediamine, 52 g of water, 6.4 g of Raney® nickel (doped with 1.5% by weight of chromium), 0.18 g (4 mmol) of potassium hydroxide, 75.1 g (0.37 mol) of butyl ethyl(2-cyanoethyl)phosphinate (produced as in Example 8) are reacted at 50° C. with hydrogen at 25 bar. After 8 hours, the autoclave is let down. For purification, the reaction solution is filtered, passed through a column charged with Deloxan® THP II and concentrated in vacuo. The product is purified by chromatography to obtain 62.0 g (81% of theory) of butyl ethyl(3-aminopropyl)phosphinate as colorless oil.

Workup

  1. customFor purification
  2. filtrationthe reaction solution is filtered
  3. additioncharged with Deloxan® THP II
  4. concentrationconcentrated in vacuo
  5. customThe product is purified by chromatography

Sources & evidence

ORD record
ord-98a05381542c4d82804e8f883736600e
Source dataset
uspto-grants-2015_05
Patent number
US09035088B2

Reaction notes

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