1,2-Dichloroethane → N'-(9H-Fluoren-9-yl)-N,N-dimethyl-1-thiophen-2-yl-cyclohexane-1,4-diamine dihydrochloride

HRID 1179064Notes

Reaction equation

HRID 1179064 reaction equation
[NH2:1][CH:2]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH3:15][N:16]([CH3:29])[C:17]1([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:48]CCCl>>[ClH:48].[ClH:48].[CH:13]1[C:14]2[CH:2]([NH:1][CH:20]3[CH2:21][CH2:22][C:17]([C:24]4[S:25][CH:26]=[CH:27][CH:28]=4)([N:16]([CH3:29])[CH3:15])[CH2:18][CH2:19]3)[C:3]3[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 10671Fluoren-9-amineHCID 5049666Sodium triacetoxyborohydrideHCID 12595637HCID 12595637, compound

Product 1

HCID 69337172N'-(9H-Fluoren-9-yl)-N,N-dimethyl-1-thiophen-2-yl-cyclohexane-1,4-diamine dihydrochloride

Procedure

362 mg 9-Aminofluorene and 434 mg 4-dimethylamino-4-thiophen-2-yl-cyclohexanone were dissolved in dry 1,2-dichloroethane (10 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. The alkaline phase was diluted with water (10 ml) and extracted with ethyl acetate (5×20 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product was chromatographed over silica gel with ethyl acetate/ethanol (1:1). 440 mg of a cis/trans mixture of N′-(9H-fluoren-9-yl)-N,N-dimethyl-1-thiophen-2-yl-cyclohexane-1,4-diamine were obtained as a white solid, from which the corresponding dihydrochloride was precipitated with 1.85 Methanolic hydrochloric acid (1.55 ml) in 2-butanone (10 ml) (460 mg; m.p. 202-205° C.).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe alkaline phase was diluted with water (10 ml)
  3. extractionextracted with ethyl acetate (5×20 ml)
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product was chromatographed over silica gel with ethyl acetate/ethanol (1:1)

Sources & evidence

ORD record
ord-8cf6a2d1c2c44ddfbce70be5785f5fae
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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