Hydrogen Bromide → HCID 12319402, compound

HRID 1077326Notes

Reaction equation

HRID 1077326 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11]3([CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[O:10]2)=[CH:5][CH:4]=1.Br.C(=O)(O)[O-].[Na+]>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11]3([CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[O:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 12319398HCID 12319398, compound

Product 1

HCID 12319402HCID 12319402, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.5 g. of 1,3-dihydro-3-(4-methoxyphenyl)-1'-methylspiro[isobenzofuran-1,4'-piperidine], (Example 12), and 20 ml. of 48% hydrobromic acid is heated under reflux, cooled, diluted with water, neutralized with sodium bicarbonate, and extracted with chloroform. The chloroform solution is dried over magnesium sulfate and concentrated to an oil. Trituration with ether provides crystals, m.p. 132°dec. Recrystallization raises the melting point to 273°dec.

Workup

  1. temperatureunder reflux
  2. temperaturecooled
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform solution is dried over magnesium sulfate
  5. concentrationconcentrated to an oil
  6. customTrituration with ether provides crystals
  7. customRecrystallization
  8. temperatureraises the melting point to 273°dec

Sources & evidence

ORD record
ord-e035f73f5e324ffcbbb6ece764fb6d8a
Source dataset
uspto-grants-1976_05
Patent number
US03959475

Reaction notes

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