Triethylamine → HCID 44185127, compound

HRID 2090815Notes

Reaction equation

HRID 2090815 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[S:17](Cl)(=[O:19])=[O:18].Cl.Cl.Cl.[CH3:24][N:25]1[CH2:30][CH2:29][CH:28]([N:31]2[CH2:36][CH2:35][N:34]([C:37](=[O:47])[CH2:38][O:39][CH2:40][CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][NH:42]3)[CH2:33][CH2:32]2)[CH2:27][CH2:26]1.C(=O)([O-])O.[Na+]>O1CCCC1>[C:11]1([CH3:16])[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([CH3:8])[C:10]=1[S:17]([N:42]1[CH2:43][CH2:44][CH2:45][CH2:46][CH:41]1[CH2:40][O:39][CH2:38][C:37]([N:34]1[CH2:33][CH2:32][N:31]([CH:28]2[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]2)[CH2:36][CH2:35]1)=[O:47])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 44185218HCID 44185218, compound

Product 1

HCID 44185127HCID 44185127, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.221 ml, 1.608 mmol) and then 2,4,6-trimethylbenzenesulfonyl chloride (105 mg, 0.482 mmol) were added at 0° C. to a solution of 1-(4-(1-methylpiperidin-4-yl)piperazin-1-yl)-2-(piperidin-2-ylmethoxy)ethanone trihydrochloride (180 mg, 0.402 mmol) in tetrahydrofuran (10 ml). The reaction mixture was heated slowly to room temperature, stirred for 15 h at that temperature and then refluxed for 1 h. Saturated sodium hydrogen carbonate solution (5 ml) was then added to the mixture, and the aqueous phase was extracted with ethyl acetate (3×30 ml). The combined organic phases were dried (Na2SO4) and concentrated in vacuo, and the crude product was then purified by column chromatography (silica gel) using ethyl acetate/methanol/ammonia solution (25% aq.) (300:100:5). Yield: 90 mg (43%), yellow oil; MS, m/z 520.3 (MH+)

Workup

  1. temperaturerefluxed for 1 h
  2. extractionthe aqueous phase was extracted with ethyl acetate (3×30 ml)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customthe crude product was then purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-f2a58cbfda9343f9a7997b93b52c0184
Source dataset
uspto-grants-2013_05
Patent number
US08435978B2

Reaction notes

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