Acetic Anhydride → HCID 2742017, compound

HRID 2197443Notes

Reaction equation

HRID 2197443 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][NH2+:15][CH2:14][CH2:13]2)[O:9][N:8]=1.C(N(C(C)C)CC)(C)C.[C:27](OC(=O)C)(=[O:29])[CH3:28]>ClCCl>[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][N:15]([C:27](=[O:29])[CH3:28])[CH2:14][CH2:13]2)[O:9][N:8]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 86654171HCID 86654171, compound

Product 1

HCID 2742017HCID 2742017, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 mg (1 eq.) of 4-(3-thiophen-2-yl[1,2,4]oxadiazol-5-yl)-piperidinium hydrochloride and 77 μl (3 eq.) of diisopropylethylamine were dissolved in 1 ml of dichloromethane. 39 μl (1.2 eq.) of acetic anhydride were added dropwise and the reaction medium was stirred for 2 hours at room temperature. The reaction medium was evaporated and the residue was taken up in 15 ml of ethyl acetate. The organic phase was washed with aqueous 1N sodium hydroxide solution (3×30 ml), with aqueous 1N hydrochloric acid solution (3×30 ml) and with saturated aqueous NaCl solution (30 ml), dried over MgSO4 and concentrated under reduced pressure to give 41 mg (98%) of the expected compound.

Workup

  1. customThe reaction medium was evaporated
  2. washThe organic phase was washed with aqueous 1N sodium hydroxide solution (3×30 ml), with aqueous 1N hydrochloric acid solution (3×30 ml) and with saturated aqueous NaCl solution (30 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-936d5ea45c3744f2a2cbbd86ce4607bb
Source dataset
uspto-grants-2012_12
Patent number
US08338599B2

Reaction notes

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