1-{4-[1-(2-Phenylethyl)-1H-imidazole-2-carbonyl]piperidin-1-yl}ethan-1-one → HCID 19371531, compound

HRID 275281Notes

Reaction equation

HRID 275281 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([C:12]2[N:13]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:14]=[CH:15][N:16]=2)=[O:11])[CH2:6][CH2:5]1)(=O)C.C(N1CCC(C(OC(=C2CCN(C(=O)C)CC2)C2N(CCC3C=CC=CC=3)C=CN=2)=O)CC1)(=O)C>Cl>[C:19]1([CH2:18][CH2:17][N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[C:10]([CH:7]2[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]2)=[O:11])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 200877541-{4-[1-(2-Phenylethyl)-1H-imidazole-2-carbonyl]piperidin-1-yl}ethan-1-oneHCID 20087755HCID 20087755, compound

Product 1

HCID 19371531HCID 19371531, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture (3.87 g) of 1-acetyl-4-[[1-(2-phenylethyl)-1H-imidazol-2yl]carbonyl]piperidine (D), (1-acetyl-4-pipendinylidene)[1-(2-phenylethyl)-1H-imidazol-2-yl]methyl 1 -acetyl-4-piperidine carboxylate (H), and 6 N hydrochloric acid (100 ml) was refluxed for 20 hrs. The cooled reaction mixture was concentrated, and the residue was diluted with water. The resulting mixture was sequentially washed with ether and ethyl acetate. The acidic aqueous layer was basified with sodium hydroxide solution and was extracted with dichloromethane. The combined extracts were washed with water, dried, filtered, and concentrated to give [1-(2-phenyethyl)-1H-imidazol-2-yl](4-piperidinyl) methanone (K, 0.91 g), m.p. 230°-232° C. from dichloromethane-hexanes. ##STR31##

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated
  3. additionthe residue was diluted with water
  4. washThe resulting mixture was sequentially washed with ether and ethyl acetate
  5. extractionwas extracted with dichloromethane
  6. washThe combined extracts were washed with water
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-21aec81edd764800914f541bc73dc18d
Source dataset
uspto-grants-1995_02
Patent number
US05393753

Reaction notes

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