Acetic Acid → 3-(p-Chlorobenzylamino)propyl(n-butyl)phosphinic acid ethyl ester

HRID 1654469Notes

Reaction equation

HRID 1654469 reaction equation
[CH2:1]([O:3][P:4]([CH2:10][CH2:11][CH2:12][NH2:13])([CH2:6][CH2:7][CH2:8][CH3:9])=[O:5])[CH3:2].[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:3][P:4]([CH2:10][CH2:11][CH2:12][NH:13][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([Cl:14])=[CH:16][CH:17]=1)([CH2:6][CH2:7][CH2:8][CH3:9])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 99905983-Aminopropyl(n-butyl)phosphinic acid ethyl ester

Product 1

HCID 537557203-(p-Chlorobenzylamino)propyl(n-butyl)phosphinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.14 g of 3-aminopropyl(n-butyl)phosphinic acid ethyl ester are mixed with 2.51 g of p-chlorobenzaldehyde, and first 1.2 g of glacial acetic acid and then a solution of 0.42 g of sodium cyanoborohydride in 5 ml of methanol are added, whereupon an exothermic reaction takes place. The mixture is then stirred at room temperature for 2.5 hours and adjusted to pH 8, and the volatile constituents are removed under reduced pressure. The residue is dissolved in dichloromethane, washed with water, dried over sodium sulfate and concentrated by evaporation. The residue is purified by chromatography on silica gel, yielding 3-(p-chlorobenzylamino)propyl(n-butyl)phosphinic acid ethyl ester; 1H-NMR spectrum (in CDCl3): δ=7.30-7.32 (4H,m); 4.02 (2H,q); 3.74 (2H,s); 2.67 (2H,t); 2.5-2.22 (1H,S); 1.79-1.64 (6H,m); 1.53 (2H,m); 1.42 (2H,m; 1.31 (3H,t); 0.81 (3H,t); 31P-NMR spectrum (in CDCl3 ): δ=58.16.

Workup

  1. customthe volatile constituents are removed under reduced pressure
  2. dissolutionThe residue is dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-cbc298347a0e49398576b470609d3490
Source dataset
uspto-grants-1995_04
Patent number
US05407922

Reaction notes

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