Sodium Bicarbonate → 1-(4-Hydroxy-4-(thiophen-2-yl)piperidin-1-yl)-2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)ethanone

HRID 2041088Notes

Reaction equation

HRID 2041088 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][O:20][CH2:21][C:22]([OH:24])=O)(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31]1([OH:37])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:37][C:31]1([C:27]2[S:26][CH:30]=[CH:29][CH:28]=2)[CH2:32][CH2:33][N:34]([C:22](=[O:24])[CH2:21][O:20][CH2:19][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][N:13]2[S:10]([C:6]2[C:5]([CH3:25])=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=2[CH3:9])(=[O:11])=[O:12])[CH2:35][CH2:36]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 14441129HCID 14441129, compoundHCID 574368002-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetic acid

Product 1

HCID 598201011-(4-Hydroxy-4-(thiophen-2-yl)piperidin-1-yl)-2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N′-Carbonyldiimidazole (68 mg, 0.424 mmol) was added to a solution of 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetic acid (acid unit S24) (150 mg, 0.404 mmol) in methylene chloride (5 ml) and the mixture was stirred for 1 h at room temperature. A solution of 4-(thiophen-2-yl)piperidin-4-ol (73 mg, 0.404 mmol) in methylene chloride (2 ml) was subsequently added and the reaction mixture was stirred for 15 h at room temperature. Thereafter, saturated sodium bicarbonate solution (10 ml) was added to the reaction mixture and the aqueous phase was subsequently extracted with methylene chloride (2×10 ml). The combined organic phases were extracted with saturated sodium chloride solution (10 ml), dried with sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography with ethyl acetate/hexane (20:1).

Workup

  1. stirringthe reaction mixture was stirred for 15 h at room temperature
  2. extractionthe aqueous phase was subsequently extracted with methylene chloride (2×10 ml)
  3. extractionThe combined organic phases were extracted with saturated sodium chloride solution (10 ml)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography with ethyl acetate/hexane (20:1)

Sources & evidence

ORD record
ord-e3b749592f5e4c5d9a1f00154df27e1d
Source dataset
uspto-grants-2013_11
Patent number
US08580965B2

Reaction notes

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