Phosphorus oxide (P4O10) → HCID 21286397, compound

HRID 2231207Notes

Reaction equation

HRID 2231207 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][CH:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C(C)=CC=CC=1>[ClH:1].[Cl:1][CH2:2][C:3]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[CH2:7][CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 14257921HCID 14257921, compound

Product 1

HCID 21286397HCID 21286397, compoundYield 131.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Solid N-chloroacetyl-1-phenyl-2-(3-methoxyphenyl)ethylamine (72.0 g, 0.23 mol) was added with stirring to a suspension of phosphorus pentoxide (261.1 g, 1.84 mol) in xylene (6 L) maintained under nitrogen at reflux, and the resulting mixture was refluxed for 1 hr, after which it was allowed to cool to ambient temperature. The xylene was decanted off and the residue was cooled to 0° C. Ice cold water (4 L) was added to the residue, and the resulting solution was then basified to pH 11 with 50% NaOH, and then extracted, first with ether (1 L) and then with chloroform (2×750 ml). The combined organic extracts were dried over MgSO4, evaporated to a dark oil which was dissolved in a mixture of acetone (200 ml) and ether (100 ml) and then acidified with HCl gas. Upon standing, the treated extracts yielded yellowish solid crystals, which were collected by filtration to give 48.8 g (64%) of 1-chloromethyl-3,4-dihydro-6-methoxy-3-phenylisoquinoline hydrochloride. An analyticl sample recrystallized from acetone had a mp. 174°-175° C.

Workup

  1. temperaturemaintained under nitrogen
  2. temperatureat reflux
  3. temperaturethe resulting mixture was refluxed for 1 hr
  4. customThe xylene was decanted off
  5. temperaturethe residue was cooled to 0° C
  6. additionIce cold water (4 L) was added to the residue
  7. extractionextracted, first with ether (1 L)
  8. dry with materialThe combined organic extracts were dried over MgSO4
  9. customevaporated to a dark oil which
  10. dissolutionwas dissolved in a mixture of acetone (200 ml) and ether (100 ml)
  11. customthe treated extracts yielded yellowish solid crystals, which
  12. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-87e6049a66ab43fc9896b085664daa35
Source dataset
uspto-grants-1988_11
Patent number
US04782058

Reaction notes

Loading…