Hydrogen Bromide → 1-Methylspiro[piperidine-4,9'-xanthen]-4'-ol

HRID 2286891Notes

Reaction equation

HRID 2286891 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][C:6]2([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([O:22]C)[C:16]=3[O:15][C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:5][CH2:4]1.Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[CH3:2][N:3]1[CH2:4][CH2:5][C:6]2([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([OH:22])[C:16]=3[O:15][C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 14570251HCID 14570251, compound

Product 1

HCID 145702601-Methylspiro[piperidine-4,9'-xanthen]-4'-ol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1'-Methyl-4-methoxyxanthene-9-spiro-4'-piperidine hydrochloride (1.0 g.) in a solution of 45% w/v hydrobromic acid in glacial acetic acid (10 ml.) is heated under reflux for 2 hours. The solution is basified with sodium bicarbonate, diluted with water and extracted with chloroform. The chloroform extract is washed with water, dried over MgSO4, and evaporated to dryness. The residue is recrystallised from toluene-petroleum ether (b.p. 60°-80° C.) to give 1'-methyl-4-hydroxyxanthene-9-spiro-4'-piperidine, m.p. 171°-173° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. washis washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe residue is recrystallised from toluene-petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-347a249b49bb46078a75b73671b597ef
Source dataset
uspto-grants-1981_05
Patent number
US04268514

Reaction notes

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