Hydrochloric Acid → HCID 178479772, compound

HRID 1863882Notes

Reaction equation

HRID 1863882 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][P:11](=[O:18])(CC2CC2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6]C=CC=1.[ClH:19]>C(O)C>[ClH:19].[CH:2]1([CH2:1][N:8]2[CH2:9][CH2:10][PH:11](=[O:18])[CH2:12][CH2:13]2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66832840HCID 66832840, compound

Product 1

HCID 178479772HCID 178479772, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The material from Step 5 was dissolved in ethanol (80 mL) and aqueous HCl (40 mL, 1 M) was added. The solution was degassed with a stream of nitrogen and palladium on carbon (10%, 1.0 g) was added. The mixture was hydrogenated on a Parr shaker overnight at 20 psi. The reaction mixture was filtered through Celite and the solvents were removed under reduced pressure. The product was dissolved in methanol, and benzene was added. The solvents were removed by rotary evaporation. The product was recrystallized from ethanol/diethyl ether to yield 3.526 g of 4-(cyclopropylmethyl-[1,4]azaphosphinane 4-oxide hydrochloride (16.83 mmol, 92%) as a white crystalline solid. 1H NMR (400 MHz, DMSO) 9.60-9.30 (d, 2H); 3.42-3.29 (m, 4H); 2.32-2.21 (m, 2H); 2.16-2.03 (m, 2H); 1.91-1.85 (d of d, 2H); 0.95-0.85 (m, 1H); 0.59-0.51 (m, 2H); 0.26-0.20 (m, 2H); ESMS (m/z): (M+1)+found, 174; (M+23)+ found, 196.

Workup

  1. customThe solution was degassed with a stream of nitrogen and palladium on carbon (10%, 1.0 g)
  2. additionwas added
  3. customwas hydrogenated on a Parr shaker overnight at 20 psi
  4. filtrationThe reaction mixture was filtered through Celite
  5. customthe solvents were removed under reduced pressure
  6. dissolutionThe product was dissolved in methanol
  7. additionbenzene was added
  8. customThe solvents were removed by rotary evaporation
  9. customThe product was recrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-ac5afe11a71c448193ad308bb5ef3d37
Source dataset
uspto-grants-2009_12
Patent number
US07625880B2

Reaction notes

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