Hydrochloric Acid → 4-Phenyl-1,4lambda5-azaphosphinan-4-one hydrochloride

HRID 1013500Notes

Reaction equation

HRID 1013500 reaction equation
C([N:8]1[CH2:13][CH2:12][P:11](=[O:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:21]>CO.[OH-].[OH-].[Pd+2]>[ClH:21].[C:14]1([P:11]2(=[O:20])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 579732961-Benzyl-4-phenyl-1,4-azaphosphinane 4-oxide

Product 1

HCID 668324724-Phenyl-1,4lambda5-azaphosphinan-4-one hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-benzyl-4-phenyl-1,4-azaphosphinane 4-oxide (1.18 g, 4.14 mmol), 20% Pd(OH)2/C (290 mg, 0.41 mmol), and concentrated HCl (0.75 mL) in MeOH (75 mL) was hydrogenated at 45 psi for 18 h. The mixture was filtered through Celite and evaporated. The solid residue was slurried in EtOAc and filtered to give the title compound as an off-white solid. 1H NMR (DMSO-d6, 600 MHz) δ 9.87 (bs, 1H), 9.28 (bs, 1H), 7.86-7.79 (m, 2H), 7.66-7.61 (m, 1H), 7.60-7.56 (m, 2H), 3.52-3.34 (m, 4H), 2.75-2.65 (m, 2H), 2.24-2.13 (m, 2H). MS: cal'd 196 (MH+), exp 196 (MH+).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-2597f65725b14beda132f1a8a79da65a
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

Loading…