1,2-Dichloroethane → N,N-Dimethyl-N'-[2-(5-methyl-1H-indol-3-yl)-ethyl]-1-phenyl-cyclohexane-1,4-diamine dihydrochloride

HRID 1179079ノート

反応式

HRID 1179079 の反応式
[CH3:1][C:2]1[CH:13]=[C:12]2[C:5]([NH:6][CH:7]=[C:8]2[CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.[CH3:14][N:15]([CH3:29])[C:16]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.O=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:46]CCCl>C(O)(=O)C.O1CCCC1>[ClH:46].[ClH:46].[CH3:14][N:15]([CH3:29])[C:16]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:17][CH2:18][CH:19]([NH:11][CH2:10][CH2:9][C:8]2[C:12]3[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:13]=3)[NH:6][CH:7]=2)[CH2:20][CH2:21]1

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 977OxygenHCID 157605-MethyltryptamineHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

生成物 1

HCID 69337474N,N-Dimethyl-N'-[2-(5-methyl-1H-indol-3-yl)-ethyl]-1-phenyl-cyclohexane-1,4-diamine dihydrochloride

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

5-Methyltryptamine (348 mg) and 4-dimethylamino-4-phenylcyclohexanone (435 mg) were dissolved in dry 1,2-dichloroethane (5 ml) and tetrahydrofuran (15 ml) with the exclusion of oxygen. Glacial acetic acid (114 μl) and sodium triacetoxyborohydride (600 mg) were added to this mixture and the mixture was stirred for 24 hours at RT. For working up, the mixture was concentrated, the residue was taken up in 1M HCl (20 ml) and diethyl ether (40 ml), the phases were separated, and the aqueous phase was extracted with diethyl ether (2×20 ml) and adjusted to pH 11 with 5M NaOH. The aqueous phase was diluted with water (10 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were dried with Na2SO4 and concentrated. The residue was purified by chromatography with MeOH/NH3 (500:1). The nonpolar diastereomer (brown oil, 379 mg) was dissolved in 2-butanone (10 ml) and converted by addition of chlorotrimethylsilane (319 μl) into the corresponding dihydrochloride (white solid; 405 mg; m.p. 234-236° C.).

後処理

  1. concentrationthe mixture was concentrated
  2. customdiethyl ether (40 ml), the phases were separated
  3. extractionthe aqueous phase was extracted with diethyl ether (2×20 ml)
  4. additionThe aqueous phase was diluted with water (10 ml)
  5. extractionextracted with ethyl acetate (3×20 ml)
  6. dry with materialThe combined organic extracts were dried with Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography with MeOH/NH3 (500:1)
  9. dissolutionThe nonpolar diastereomer (brown oil, 379 mg) was dissolved in 2-butanone (10 ml)
  10. additionconverted by addition of chlorotrimethylsilane (319 μl) into the corresponding dihydrochloride (white solid; 405 mg; m.p. 234-236° C.)

出典と根拠

ORDレコード
ord-2a5c60e9291b4a0cb1e4c384f503689c
出典データセット
uspto-grants-2007_10
特許番号
US07276518B2

反応ノート

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