Hydrochloric Acid → HCID 70579035, compound

HRID 2286893Notes

Reaction equation

HRID 2286893 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[C:15]([C:16]4([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3.Br[CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26].C(=O)(O)[O-].[Na+].[ClH:33]>C(O)(C)C.O.CN(C)C=O>[ClH:33].[CH3:26][C:25]([CH3:27])=[CH:24][CH2:23][N:19]1[CH2:20][CH2:21][C:16]2([C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[O:9][C:10]3[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:17][CH2:18]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 700922-Butene, 1-bromo-3-methyl-HCID 516892Sodium BicarbonateHCID 70576880HCID 70576880, compound

Product 1

HCID 70579035HCID 70579035, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-methoxyxanthene-9-spiro-4'-piperidine (2.0 g.), 1-bromo-3-methylbut-2-ene (1.15 g.), sodium bicarbonate (0.59 g.) and dimethylformamide (20 ml.) is heated under reflux for 4 hours. The mixture is cooled, poured into water and extracted with chloroform. The chloroform extract is washed with water, dried with MgSO4 and evaporated to give a gummy residue. The residue is dissolved in isopropanol and treated with ethereal hydrochloric acid. The residue is recrystallised from isopropanol-ether to give 1'-(3-methylbut-2-enyl)-4-methoxyxanthene-9-spiro-4'-piperidine hydrochloride, m.p. 247°-249° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. temperatureThe mixture is cooled
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. washis washed with water
  7. dry with materialdried with MgSO4
  8. customevaporated
  9. customto give a gummy residue
  10. customThe residue is recrystallised from isopropanol-ether

Sources & evidence

ORD record
ord-c123d412dcb9466d83160f72c891f5d4
Source dataset
uspto-grants-1981_05
Patent number
US04268514

Reaction notes

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