Hydrochloric Acid → HCID 14570249、化合物

HRID 1414544ノート

反応式

HRID 1414544 の反応式
[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

参加物

9

反応物 5

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

生成物 1

HCID 14570249HCID 14570249、化合物

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒3 回HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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 now 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.

後処理

  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

出典と根拠

ORDレコード
ord-e07492e14af04e94a1abc6d7df9085ac
出典データセット
uspto-grants-1977_01
特許番号
US04001419

反応ノート

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