Hydrogen Bromide → HCID 21493373, compound

HRID 1973282Notes

Reaction equation

HRID 1973282 reaction equation
[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][C:9]2([C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20]C)[CH:18]=3)[CH:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:12]2)[CH2:8][CH2:7]1)([CH3:4])=[O:3].Br.C(=O)(O)[O-].[Na+]>O>[CH3:4][P:2]([CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([C:19]3[C:14](=[CH:15][CH:16]=[C:17]([OH:20])[CH:18]=3)[CH:13]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:12]2)[CH2:10][CH2:11]1)([CH3:1])=[O:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 21493376HCID 21493376, compound

Product 1

HCID 21493373HCID 21493373, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1,3-dihydro-1'-dimethylphosphinylmethyl-6-methoxy-3-phenylspiro[isobenzofuran-1,4'-piperidine] and 48% hydrobromic acid is heated under reflux, cooled, diluted with water, neutralized with sodium bicarbonate and extracted with chloroform. The chloroform solution is dried and the chloroform evaporated off, affording 1,3-dihydro-1'-dimethylphosphinylmethyl-6-hydroxy-3-phenylspiro[isobenzofuran-1,4'-piperidine]. In an analogous manner, 1,3-dihydro-1'-dimethylphosphinylmethyl-5-methoxy-3-phenylspiro[isobenzofuran-1,4'-piperidine] and 1,3-dihydro-1'-dimethylphosphinylmethyl-3-(4-methoxyphenyl)spiro[isobenzofuran-1,4'-piperidine] are treated to provide 1,3-dihydro-1'-dimethylphosphinylmethyl-5-hydroxy-3-phenylspiro[isobenzofuran-1,4'-piperidine] and 1,3-dimethylphosphinylmethyl-3-(4-hydroxyphenyl)spiro[isobenzofuran-1,4'-piperidine], respectively.

Workup

  1. temperatureunder reflux
  2. temperaturecooled
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform solution is dried
  5. customthe chloroform evaporated off

Sources & evidence

ORD record
ord-945c29ecbb5b44939610ed84f19aded4
Source dataset
uspto-grants-1976_12
Patent number
US03996354

Reaction notes

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