1,2-Dichloroethane → HCID 86594055, compound

HRID 1179068Notes

Reaction equation

HRID 1179068 reaction equation
[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

Participants

7

Reactant 5

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

Product 2

HCID 86594055HCID 86594055, compoundHCID 87789295HCID 87789295, compound

Procedure

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.).

Workup

  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)

Sources & evidence

ORD record
ord-31982095a6334a429692fd8f631e54a0
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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