Hydrochloric Acid → Ethyl 3-amino-3-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate

HRID 1165320Notes

Reaction equation

HRID 1165320 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([CH2:8][CH2:9][P:10]([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])(=[O:14])[O:11][CH2:12][CH3:13])=O)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:30].[Na+].Cl>CO>[NH2:30][CH:6]([C:5]1[CH:22]=[CH:23][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:8][CH2:9][P:10]([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])(=[O:14])[O:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 14362821Ethyl 2-(4-chlorobenzoyl)ethyl(diethoxymethyl)phosphinate

Product 1

HCID 14362823Ethyl 3-amino-3-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 25.4 g of ethyl 2-(4-chlorobenzoyl)ethyl(diethoxymethyl)phosphinate in 200 ml of methanol is added 52 g of ammonium acetate and 4.23 g of sodium cyanoborohydride. The mixture is stirred under an atmosphere of nitrogen at room temperature for a period of 3 days. The mixture is then acidified to pH 2 with the requisite amount of dilute hydrochloric acid and the methanol is evaporated under reduced pressure. The crude product is dissolved in 25 ml of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then made alkaline to pH 12 with potassium hydroxide. The solution is then saturated with sodium chloride and extractd with 3×25 ml of dichloromethane. The organic phase is dried over magnesium sulphate and then evaporated under reduced pressure to give ethyl 3-amino-3-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate as a viscous oil, 31P=45.9 ppm (CDCl3).

Workup

  1. customthe methanol is evaporated under reduced pressure
  2. dissolutionThe crude product is dissolved in 25 ml of water
  3. washwashed twice with 20 ml of diethyl ether
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a59500449128466f8c6386b4439124b5
Source dataset
uspto-grants-1990_03
Patent number
US04908465

Reaction notes

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