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

HRID 562401Notes

Reaction equation

HRID 562401 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]>CCO.[Pd]>[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 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Benzyl-4-phenyl-[1,4]azaphosphinane 4-oxide (14.2 g, 49.8 mmol) was dissolved in absolute EtOH (65 mL) and 1N HCl (50 mL). Palladium on carbon (10%, 2.0 g) was added and the mixture was hydrogenated on a Parr shaker at 50 psi for 60 hours. After filtration through Celite, the filtrate was rotovapped and the residue was triturated with ether to give 4-phenyl-[1,4]azaphosphinane 4-oxide hydrochloride, as an off-white solid (11.40 g, 99%). 1H NMR (400 MHz, DMSO-d6) δ 7.85 (m, 2H), 7.65 (m, 3H), 3.5 (m, 4H), 2.7 (m, 2H), 2.2 (broad t, 2H). 31P NMR (DMSO-d6); δ 24.0 (s).

Workup

  1. filtrationAfter filtration through Celite
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-434bf8ed75d54b528c722febfd417b10
Source dataset
uspto-grants-2011_11
Patent number
US08067395B2

Reaction notes

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