1,2-Dichloroethane → HCID 86594055、化合物

HRID 1179068ノート

反応式

HRID 1179068 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[CH3:16][N:17]([CH3:31])[C:18]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:50]CCCl>>[CH:3]1[C:4]2[C:13](=[CH:12][C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:14]=[CH:15][C:2]=1[NH:1][CH:21]1[CH2:20][CH2:19][C:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([N:17]([CH3:31])[CH3:16])[CH2:23][CH2:22]1.[ClH:50].[CH:3]1[C:4]2[C:13](=[CH:12][C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:14]=[CH:15][C:2]=1[NH:1][CH:21]1[CH2:20][CH2:19][C:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([N:17]([CH3:31])[CH3:16])[CH2:23][CH2:22]1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 119372-AminoanthraceneHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

生成物 2

HCID 86594055HCID 86594055、化合物HCID 87789295HCID 87789295、化合物

実験手順

386 mg 2-Aminoanthracene and 434 mg 4-dimethylamino-4-phenyl-cyclohexanone were dissolved in dry 1,2-dichloroethane (20 ml) under argon. Glacial acetic acid (2 mmol) and 600 mg sodium triacetoxyborohydride were added to this mixture and the mixture was stirred for 24 hours at RT. For working up, the reaction mixture was concentrated and the residue was adjusted to pH 11 with five molar sodium hydroxide solution and extracted with ethyl acetate (4×20 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude products was chromatographed over silica gel with ethyl acetate/ethanol (1:1). 132 mg of the nonpolar diastereomer of N′-anthracen-2-yl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a green solid, from which the corresponding hydrochloride was precipitated with 1.85 M ethanolic hydrochloric acid (0.46 ml) in 2-butanone (5 ml) (104 mg; m.p. 169-172° C.).

後処理

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate (4×20 ml)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe crude products was chromatographed over silica gel with ethyl acetate/ethanol (1:1)

出典と根拠

ORDレコード
ord-31982095a6334a429692fd8f631e54a0
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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