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

HRID 1654470Notes

Reaction equation

HRID 1654470 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 point 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-cbc7747ad846450dbe0f52bdb430fef3
Source dataset
uspto-grants-1995_04
Patent number
US05407922

Reaction notes

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