Water → HCID 23112206, compound

HRID 2264314Notes

Reaction equation

HRID 2264314 reaction equation
BrC[CH2:3][C:4]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][C:5]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[N:21]1([CH2:3][C:4]2[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][C:5]=2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 68704561HCID 68704561, compound

Product 1

HCID 23112206HCID 23112206, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 50 ml of DMF was dissolved 13.6 g of ethyl 2-(bromoethyl)biphenyl-4-carboxylate, and then a suspension of 50 ml of DMF, 6.2 ml of piperidine, and 9.2 g of potassium carbonate were added thereto under ice cooling, followed by 3 hours of stirring at room temperature. Water was added to the reaction solution, the whole was extracted with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, followed by removal of the solvent by evaporation. The obtained residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia) to obtain 12.6 g of ethyl 2-(piperidin-1-ylmethyl)biphenyl-4-carboxylate as a pale yellow oil.

Workup

  1. additionwere added
  2. extractionthe whole was extracted with ethyl acetate
  3. dry with materialthe resulting organic layer was dried over anhydrous magnesium sulfate
  4. customfollowed by removal of the solvent by evaporation
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia)

Sources & evidence

ORD record
ord-f05a74b16e394a489ad6020c466d9c49
Source dataset
uspto-grants-2010_12
Patent number
US07855198B2

Reaction notes

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