Ethanol → 3-biphenyl-4-yl-N-[3-chloro-4-(2-diethylaminoethoxy)phenyl]-3-oxopropionamide

HRID 1820871Notes

Reaction equation

HRID 1820871 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:32])[C:18]#[C:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13].N1CCCCC1.C([OH:41])C>CCOCC>[C:23]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:22]=[CH:21][C:20]([C:19](=[O:41])[CH2:18][C:17]([NH:16][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[C:2]([Cl:1])[CH:3]=2)=[O:32])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8082PiperidineHCID 57845845HCID 57845845, compound

Product 1

HCID 112712463-biphenyl-4-yl-N-[3-chloro-4-(2-diethylaminoethoxy)phenyl]-3-oxopropionamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.16 g (0.36 mmol) of 3-biphenyl-4-ylpropynoic acid-[3-chloro-4-(2-diethylaminoethoxy)phenyl]amide (educt XII.1) is dissolved in 10 mL of aqueous ethanol and 0.10 mL (1.0 mmol) of piperidine is added. The mixture is stirred for 8 hours at reflux temperature. After cooling, the solvent is eliminated, and the residue is suspended in ether and filtered off. The residue is dried in vacuo at 50° C. Yield: 75 mg (45% of theory); Rf value: 0.40 (silica gel, methylene chloride/methanol/ammonia=9:1:0.01); m.p. 148° C.-151° C.; C27H29ClN2O3; EII mass spectrum: m/z=465/467 [M+H]+.

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationfiltered off
  4. customThe residue is dried in vacuo at 50° C

Sources & evidence

ORD record
ord-59e7b0443acd4610a5b6ec0e3220a01e
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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