Hydrochloric Acid → N'-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine dihydrochloride

HRID 1179078

反応式

HRID 1179078 の反応式
CO[C:3]1[CH:4]=[C:5]2[C:12](=[CH:13][CH:14]=1)[C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][NH:6]2.[CH3:15][N:16]([CH3:30])[C:17]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=[O:33])C.[Na+].[ClH:45]>ClCCCl.C1COCC1.O.C(O)(=O)C>[ClH:45].[ClH:45].[CH3:31][O:33][C:14]1[CH:13]=[C:12]2[C:5](=[CH:4][CH:3]=1)[NH:6][CH:7]=[C:8]2[CH2:9][CH2:10][NH:11][CH:20]1[CH2:21][CH2:22][C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([N:16]([CH3:30])[CH3:15])[CH2:18][CH2:19]1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 176542-(2-Aminoethyl)-5-methoxyindoleHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

生成物 1

HCID 69338067N'-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine dihydrochloride

試薬・触媒・溶媒 4

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

6-Methoxytryptamine (495 mg) was dissolved until clear in dry 1,2-dichloroethane and THF (5 ml/15 ml) under argon. After addition of 4-dimethylamino-4-phenylcyclohexanone (565 mg) and glacial acetic acid (148 μl), stirring was carried out for two hours at RT, before sodium triacetoxyborohydride (858 mg) was added. The reaction mixture was stirred for two days at RT. For working up, water (15 ml) and 5.5M HCl (1.5 ml) were added to the reaction mixture. The phases were separated, the aqueous phase (pH 3) was washed with diethyl ether (3×10 ml) and then brought to pH 11 with 1M NaOH and extracted with ethyl acetate (5×15 ml). The combined extracts were dried with Na2SO4 and concentrated. The residue that remained (1.0 g; m.p. 129-153° C.) was purified by flash chromatography (eluant: MeOH/NEt3 99.25:0.75). The nonpolar diastereomer (550 mg, m.p. 164-169° C.) was separated off cleanly, dissolved in 2-butanone/acetone (15 ml/16 ml) while warm, and converted with chlorotrimethylsilane (533 μl) into the corresponding dihydrochloride (white solid; 633 mg; m.p. 165-175° C.).

後処理

  1. additionwas added
  2. stirringThe reaction mixture was stirred for two days at RT
  3. customThe phases were separated
  4. washthe aqueous phase (pH 3) was washed with diethyl ether (3×10 ml)
  5. extractionextracted with ethyl acetate (5×15 ml)
  6. dry with materialThe combined extracts were dried with Na2SO4
  7. concentrationconcentrated
  8. customwas purified by flash chromatography (eluant: MeOH/NEt3 99.25:0.75)
  9. customThe nonpolar diastereomer (550 mg, m.p. 164-169° C.) was separated off cleanly
  10. dissolutiondissolved in 2-butanone/acetone (15 ml/16 ml)
  11. temperaturewhile warm

出典と根拠

ORDレコード
ord-86590fedebab41b790012653a5ede8fa
出典データセット
uspto-grants-2007_10
特許番号
US07276518B2

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