Hydrochloric Acid → HCID 13574654, compound

HRID 236078Notes

Reaction equation

HRID 236078 reaction equation
[C:1]1([P:7]2[C:12]([CH3:14])([CH3:13])[CH2:11][C:10](=O)[CH2:9][C:8]2([CH3:17])[CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]([NH2:21])[CH2:19][CH3:20].[B-]C#N.[Na+].Cl>CO>[CH2:18]([NH:21][CH:10]1[CH2:11][C:12]([CH3:14])([CH3:13])[P:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([CH3:17])([CH3:16])[CH2:9]1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7852PropylamineHCID 41304594-Phosphorinanone, 2,2,6,6-tetramethyl-1-phenyl-HCID 20587905Sodium cyanoborohydride [MI]

Product 1

HCID 13574654HCID 13574654, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask, under nitrogen, was charged with a mixture of 12.4 grams (0.05 mole) of 1-phenyl-2,2,6,6-tetra methyl-4-phosphorinanone, 17.7 grams (0.30 mole) of n-propylamine, 1.89 grams (0.03 mole) of sodium cyanotrihydroborate, 20 mls of 5N methanolic hydrochloric acid and 150 mls of methanol. The mixture was stirred at ambient temperature for three days and then treated with 20 mls of conc. hydrochloric acid. The reaction mixture was concentrated in vacuo and 30 mls of water and 25 mls of diethylether were added. The layers were separated and to the aqueous layer was added 8 grams of solid sodium hydroxide. The resultant basic mixture was extracted sequentially with five 25 ml portions of diethylether. The combined extracts were dried over anhydrous sodium sulfate, the solvent removed in vacuo and the residue distilled under reduced pressure to give 11.2 grams (77% yield) of colorless liquid, b.p. 140°-144° C. (0.1 mm Hg)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and 30 mls of water and 25 mls of diethylether
  2. additionwere added
  3. customThe layers were separated and to the aqueous layer
  4. additionwas added 8 grams of solid sodium hydroxide
  5. extractionThe resultant basic mixture was extracted sequentially with five 25 ml portions of diethylether
  6. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  7. customthe solvent removed in vacuo
  8. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-366d33aca76f4ad8871129db13bb37b9
Source dataset
uspto-grants-1987_02
Patent number
US04642382

Reaction notes

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