Hydrochloric Acid → HCID 14570249, compound

HRID 2286886Notes

Reaction equation

HRID 2286886 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Na].[H-].[Na+].[CH3:18][N:19]([CH2:23][CH2:24]Cl)[CH2:20][CH2:21][Cl:22].Cl>CS(C)=O.CCOCC.O>[ClH:22].[CH3:18][N:19]1[CH2:23][CH2:24][C:13]2([C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[O:6][C:5]3[C:14]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH2:21][CH2:20]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4033MechlorethamineHCID 7107XantheneHCID 24758Sodium hydrideHCID 5360545Sodium

Product 1

HCID 14570249HCID 14570249, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of xanthene (9.1 g.) in dimethyl sulphoxide (75 ml.) is added dropwise over 20 minutes at room temperature to a solution of sodium methylsulphinylmethide [prepared in the usual way from sodium hydride (8 g. of a 60% dispersion in mineral oil) and dimethyl sulphoxide (100 ml.)] with stirring in an atmosphere of nitrogen. The blood-red mixture is stirred at room temperature for a further 30 minutes, cooled to 0° C., and a solution of N-methyldi-(2-chloroethyl)amine (9.6 g.) in dimethyl sulphoxide (20 ml.) is then added dropwise during 15 minutes, keeping the temperature below 20° C. Water (500 ml.) is added to the new colourless mixture, and the mixture is extracted three times with ether. The combined ether extracts are dried over MgSO4, evaporated to dryness and the gummy residue (12.2 g.) is chromatographed on basic alumina (Brockmann Grade III), eluting with increasing concentrations of chloroform in light petroleum (b.p. 60°-80° C.). Elution with 5% chloroform in light petroleum gives, on evaporation of the solvent, a gum which is dissolved in ether and treated with ethereal hydrochloric acid. The solid is recrystallised from ethanol-ether to give 1'-methylxanthene-9-spiro-4'-piperidine hydrochloride, m.p. 220°-222° C.

Workup

  1. temperaturecooled to 0° C.
  2. customthe temperature below 20° C
  3. extractionthe mixture is extracted three times with ether
  4. dry with materialThe combined ether extracts are dried over MgSO4
  5. customevaporated to dryness
  6. customthe gummy residue (12.2 g.) is chromatographed on basic alumina (Brockmann Grade III)
  7. washeluting
  8. temperaturewith increasing concentrations of chloroform in light petroleum (b.p. 60°-80° C.)
  9. washElution with 5% chloroform in light petroleum
  10. customgives, on evaporation of the solvent
  11. customThe solid is recrystallised from ethanol-ether

Sources & evidence

ORD record
ord-06d827f65a3b429cb7fd40583c0db1ea
Source dataset
uspto-grants-1981_05
Patent number
US04268514

Reaction notes

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