Acetic Anhydride → HCID 71522487, compound

HRID 2178535Notes

Reaction equation

HRID 2178535 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH:7]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]2=[O:26])[CH2:8]1.C(N(CC)CC)C.[C:34](OC(=O)C)(=[O:36])[CH3:35]>C(OCC)C>[C:34]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH:7]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]2=[O:26])[CH2:8]1)(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 89500554HCID 89500554, compound

Product 1

HCID 71522487HCID 71522487, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-(2-{2-[3-(piperidin-2-yl)pyrrolidin-1-yl]ethyl}phenyl)piperidin-2-one a12-1 (25 mg, 0.070 mmol, 1 eq) in diethylether (2 ml) at 0° C. are added triethylamine and acetic anhydride (7 μl, 0.077 mmol, 1.1 eq). The mixture is stirred for 1 hour at room temperature. The solvent is removed under vacuum. The residue obtained is purified by basic reverse phase chromatography (gradient: acetonitrile/H2O/ammonium formate from 5% to 95% of acetonitrile in 8 minutes) to afford 14.5 mg of 1-(2-{2-[3-(1-acetylpiperidin-2-yl)pyrrolidin-1-yl]ethyl}phenyl)piperidin-2-one 72 as a yellow oil.

Workup

  1. customThe solvent is removed under vacuum
  2. customThe residue obtained
  3. customis purified by basic reverse phase chromatography (gradient: acetonitrile/H2O/ammonium formate from 5% to 95% of acetonitrile in 8 minutes)

Sources & evidence

ORD record
ord-a3902debe5bf410596e39ffbc8c00842
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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