Benzylamine → HCID 15341923, compound

HRID 364610Notes

Reaction equation

HRID 364610 reaction equation
Cl[CH2:2][P:3](=[O:6])([CH3:5])[CH3:4].[CH2:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)C>[CH2:7]([NH:14][CH2:2][P:3](=[O:6])([CH3:5])[CH3:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 74224Phosphine oxide, (chloromethyl)dimethyl-

Product 1

HCID 15341923HCID 15341923, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 316.3 g of chloromethyl-dimethylphosphine oxide, 547 ml of benzylamine and 500 ml of ethanol is refluxed for 18 hours. After cooling to 20° to 25° C., the turbid suspension is filtered; the clear filtrate is then concentrated by evaporation, and to the residue are added 500 ml of 10% sodium chloride solution. The aqueous solution is extracted 4 times with 500 ml of methylene chloride each time; and the combined organic phases are subsequently dried over sodium sulfate and concentrated by evaporation. Vacuum distillation of the oily crude product yields 311.0 g (63% of theory) of N-benzyl-P,P-dimethyl-aminomethylphosphine oxide in the form of yellowish oil, b.p. 150° C./0.2 mb.

Workup

  1. temperatureAfter cooling to 20° to 25° C.
  2. filtrationthe turbid suspension is filtered
  3. concentrationthe clear filtrate is then concentrated by evaporation
  4. additionto the residue are added 500 ml of 10% sodium chloride solution
  5. extractionThe aqueous solution is extracted 4 times with 500 ml of methylene chloride each time
  6. dry with materialand the combined organic phases are subsequently dried over sodium sulfate
  7. concentrationconcentrated by evaporation
  8. distillationVacuum distillation of the oily crude product

Sources & evidence

ORD record
ord-684acfd8efc2476e83d5273bb77334ef
Source dataset
uspto-grants-1986_08
Patent number
US04605434

Reaction notes

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