Acetic Acid → HCID 69338080, compound

HRID 1179057Notes

Reaction equation

HRID 1179057 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][NH2:11])=[CH:2]1.[CH3:12][N:13]([CH3:27])[C:14]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.[C:28](O)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[CH3:12][N:13]([CH3:27])[C:14]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:18][CH:17]([NH:11][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:1]([CH3:28])[CH:2]=2)[CH2:16][CH2:15]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 24436Sodium SulfateHCID 4721071H-Indol-3-YlmethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 69338080HCID 69338080, compoundYield 5.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

450 mg C-(1H-indol-3-yl)-methylamine were partly dissolved in dry 1,2-dichloroethane (10 ml) under argon. After addition of 609 mg 4-dimethylamino-4-phenylcyclohexanone, glacial acetic acid (5.6 mmol), sodium sulfate (2 g) and sodium triacetoxyborohydride (770 mg), the suspension was stirred for five days at room temperature. For working up, water (20 ml) was added to the reaction mixture. The organic phase was separated off and the aqueous phase was washed twice with ether (5 ml) and then rendered strongly alkaline with sodium hydroxide solution. It was extracted with ether (2×5 ml) and ethyl acetate (4×10 ml), the combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product obtained was chromatographed over silica gel with methanol/triethylamine (100:1). 52 mg N,N-dimethyl-N′-(1-methyl-1H-indol-3-ylmethyl)-1-phenyl-cyclohexane-1,4-diamine were obtained as a cis/trans mixture.

Workup

  1. customThe organic phase was separated off
  2. washthe aqueous phase was washed twice with ether (5 ml)
  3. extractionIt was extracted with ether (2×5 ml) and ethyl acetate (4×10 ml)
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product obtained
  8. customwas chromatographed over silica gel with methanol/triethylamine (100:1)

Sources & evidence

ORD record
ord-09ebfc9bcbb548adb020c6ef128068bb
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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