2-Chloroacetophenone → HCID 86688951, compound

HRID 404691Notes

Reaction equation

HRID 404691 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[N:11]1([CH:17]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(OCC)(=O)C.C(#N)C>[Cl-:1].[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][N+:23]12[CH2:24][CH2:25][CH:26]([CH2:27][CH2:28]1)[C@@H:21]([O:20][C:18](=[O:19])[CH:17]([N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[C:29]1[S:30][CH:31]=[CH:32][CH:33]=1)[CH2:22]2

Participants

5

Reactant 2

HCID 107572-ChloroacetophenoneHCID 86688950HCID 86688950, compound

Product 1

HCID 86688951HCID 86688951, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (63.0 mg, 0.41 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(piperidin-1-yl)-2-(thiophen-2-yl)acetate (124 mg, 0.37 mmol) in ethyl acetate (2.5 ml) and acetonitrile (1.2 ml). The pale yellow solution was stirred at room temperature for 24 hours. The solvent was evaporated and the residue was triturated with Et2O (8 ml). The suspension was filtered on a buckner funnel washing with Et2O (5 ml) and the solid was recovered from the filter to collect the title compound (88 mg, 48.5% yield) as a off-white solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O (8 ml)
  3. filtrationThe suspension was filtered on a buckner funnel
  4. washwashing with Et2O (5 ml)
  5. customthe solid was recovered from the
  6. filtrationfilter

Sources & evidence

ORD record
ord-867f3b8a9df6478eb927bcdd8326127e
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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