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

HRID 1414548Notes

Reaction equation

HRID 1414548 reaction equation
Cl.C[O:3][C:4]1[C:9]2[O:10][C:11]3[C:16]([C:17]4([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[C:8]=2[CH:7]=[CH:6][CH:5]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3.Br.[C:24](=O)(O)[O-].[Na+]>C(O)(=O)C.O>[CH3:24][N:20]1[CH2:19][CH2:18][C:17]2([C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([OH:3])[C:9]=3[O:10][C:11]3[C:16]2=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 86734378HCID 86734378, 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-dec151fc24954db18a0175e949672b12
Source dataset
uspto-grants-1977_01
Patent number
US04001419

Reaction notes

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