Potassium Carbonate → HCID 58737423, compound

HRID 1160356Notes

Reaction equation

HRID 1160356 reaction equation
[CH2:1]([C@H:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[O:18].C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:17](=[O:18])[CH2:16][N:11]2[CH2:12][CH2:13][CH2:14][C@H:9]([CH2:1][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:10]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromideHCID 58737387HCID 58737387, compound

Product 1

HCID 58737423HCID 58737423, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (S)-3-phenethyl-piperidine (4.23 mmol, 801 mg), 2-bromo-4′-chloroacetophenone (1.5 equiv, 6.35 mmol, 1.48 g) and K2CO3 (2.0 equiv, 8.46 mmol, 1.17 g) in CH3CN (10 mL) was heated to 60° C. and stirred for 12 h. The reaction mixture was quenched with H2O (25 mL) and then extracted with EtOAc (2×50 mL). The combined organics were dried with NaCl(sat) and Na2SO4(s). The solvents were removed in vacuo and chromatography (Isco Combi-Flash, 110 g cartridge, 9:1 Hexane-EtOAc) provided the desired product (0.556 mg, 1.45 mg theoretical, 38%) as a colorless oil: Rf 0.37 (SiO2, 5:1 hexane-EtOAc); LRMS m/z 342 (M++1, C21H24ClNO, requires 342).

Workup

  1. customThe reaction mixture was quenched with H2O (25 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. dry with materialThe combined organics were dried with NaCl(sat) and Na2SO4(s)
  4. customThe solvents were removed in vacuo and chromatography (Isco Combi-Flash, 110 g cartridge, 9:1 Hexane-EtOAc)

Sources & evidence

ORD record
ord-94e01ff8e0364080b9b3a7a9a13a194a
Source dataset
uspto-grants-2010_10
Patent number
US07816375B2

Reaction notes

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