Bromotrimethylsilane → 3-(p-Chlorobenzylamino)propyl(tetrahydrofuran-2-yl)phosphinic acid hydrochloride

HRID 1077700Notes

Reaction equation

HRID 1077700 reaction equation
C[Si](C)(C)Br.C([O:8][P:9]([CH2:16][CH2:17][CH2:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)([CH:11]1[CH2:15][CH2:14][CH2:13][O:12]1)=[O:10])C>>[ClH:27].[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:19][CH2:18][CH2:17][CH2:16][P:9]([CH:11]2[CH2:15][CH2:14][CH2:13][O:12]2)(=[O:8])[OH:10])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 76113BromotrimethylsilaneHCID 544480033-(p-Chlorobenzylamino)propyl(tetrahydrofuran-2-yl)phosphinic acid ethyl ester

Product 1

HCID 217491233-(p-Chlorobenzylamino)propyl(tetrahydrofuran-2-yl)phosphinic acid hydrochloride

Procedure

0.38 g of trimethylbromosilane is added to a solution of 0.41 g of 3-(p-chlorobenzylamino)propyl(tetrahydrofuran-2-yl)phosphinic acid ethyl ester, the mixture is stirred at room temperature for 24 hours, and the volatile constituents are removed under reduced pressure. The oil that remains is taken up in 99% methanol, stirred for 30 minutes at room temperature and again concentrated by evaporation under reduced pressure. Recrystallisation of the solid yellowish residue yields 3-(p-chlorobenzylamino)propyl(tetrahydrofuran-2-yl)phosphinic acid hydrochloride having a melting pint of 212°-213°; 1H--NMR spectrum (in CD3OD): δ=7.5 (4H,m), 4.21 (2H,s), 4.03 (1H,ABq), 3.84 (2H,t,d), 3.17 (2H,t), 2.30-1.83 (8H,m); 31P--NMR spectrum (in CD3OD): δ=49.4.

Workup

  1. customthe volatile constituents are removed under reduced pressure
  2. stirringstirred for 30 minutes at room temperature
  3. concentrationagain concentrated by evaporation under reduced pressure
  4. customRecrystallisation of the solid yellowish residue

Sources & evidence

ORD record
ord-cc6672dd32754e1aa09edccf1073c1b1
Source dataset
uspto-grants-1996_08
Patent number
US05545631

Reaction notes

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