Potassium Carbonate → HCID 23102773, compound

HRID 969545Notes

Reaction equation

HRID 969545 reaction equation
[C:1]([C:3]1([N:16]2[CH2:21][CH2:20][CH:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=3)[CH2:18][CH2:17]2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#N.C[Mg]Br.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[Cl:29])[O:22][CH:19]1[CH2:18][CH2:17][N:16]([C:3]2([CH3:1])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:5][CH2:4]2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23102737HCID 23102737, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 23102773HCID 23102773, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1-Dimethylethyl 4′-cyano-4-(3,4-dichlorophenoxy)-[1,4′-bipiperidine]-1′-carboxylate (100 mg) was dissolved in THF (6 ml). Methyl magnesium bromide (3M in ether, 220 μl) was added and the mixture was stirred at RT for 2 h. Further methyl magnesium bromide (220 μl) was added and the solution was stirred for a further 60 h. Potassium carbonate solution (saturated aqueous) was added and the mixture was extracted with DCM. The organic phase was dried, filtered and evaporated to give the subtitle compound (100 mg; MS [M+H]+ (APCI+) 443/445).

Workup

  1. stirringthe solution was stirred for a further 60 h
  2. extractionthe mixture was extracted with DCM
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ec861b525a554c24aa78fee65d28a4d7
Source dataset
uspto-grants-2007_12
Patent number
US07307090B2

Reaction notes

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