Acetic Acid → HCID 57837728, compound

HRID 731930Notes

Reaction equation

HRID 731930 reaction equation
O=[CH:2][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)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)(Cl)Cl.O>[N:21]1([CH2:2][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:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 23112211HCID 23112211, compound

Product 1

HCID 57837728HCID 57837728, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

In 20 ml of 1,2-dichloroethane was dissolved 1.06 g of ethyl 2-(2-oxoethyl)biphenyl-4-carboxylate, and then 3.95 ml of piperidine, 589 μl of acetic acid, and 1.09 g of sodium triacetoxyborohydride were added thereto, followed by 3 hours of stirring. Water and chloroform were added to the reaction solution, and the organic layer obtained by an operation of separation 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 1.3 g of oily ethyl 2-(piperidin-1-ylethyl)biphenyl-4-carboxylate.

Workup

  1. customthe organic layer obtained by an operation of separation
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. customfollowed by removal of the solvent by evaporation
  4. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia)

Sources & evidence

ORD record
ord-36cff99a8f354532a6e9dd93fbf574f0
Source dataset
uspto-grants-2009_09
Patent number
US07585878B2

Reaction notes

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