1,2-Dichloroethane → HCID 178482560, compound

HRID 1179062Notes

Reaction equation

HRID 1179062 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][N:7]=[N:8][C:4]=2[CH:3]=1.[CH3:11][N:12]([CH3:26])[C:13]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:45]CCCl>>[N:6]1[C:5]2[CH:9]=[CH:10][C:2]([NH:1][CH:16]3[CH2:15][CH2:14][C:13]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)([N:12]([CH3:26])[CH3:11])[CH2:18][CH2:17]3)=[CH:3][C:4]=2[NH:8][N:7]=1.[ClH:45].[N:6]1[C:5]2[CH:9]=[CH:10][C:2]([NH:1][CH:16]3[CH2:15][CH2:14][C:13]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)([N:12]([CH3:26])[CH3:11])[CH2:18][CH2:17]3)=[CH:3][C:4]=2[NH:8][N:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneHCID 178507366HCID 178507366, compound

Product 2

HCID 178482560HCID 178482560, compoundHCID 178482561HCID 178482561, compound

Procedure

268 mg 5-Aminobenzotriazole and 435 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. The alkaline phase was diluted with water (10 ml) and extracted with ethyl acetate (3×20 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). 135 mg of the nonpolar diastereomer of N′-(3H-benzotriazol-5-yl)-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a white solid, from which the corresponding hydrochloride was precipitated with 1.85 M ethanolic hydrochloric acid (0.54 ml) in 2-butanone (5 ml) (98 mg; m.p. 168-173° C.).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe alkaline phase was diluted with water (10 ml)
  3. extractionextracted with ethyl acetate (3×20 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-3a976a979e4e420caf5ffae903c52a7d
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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