Dichloromethane → HCID 10205057, compound

HRID 1828609Notes

Reaction equation

HRID 1828609 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C[Al](C)C.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1[N:21]=[C:22]([C:33](OCC)=[O:34])[N:23]([CH3:32])[C:24]=1[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1.C(Cl)Cl>C1(C)C=CC=CC=1.CCCCCC>[N:2]1([NH:1][C:33]([C:22]2[N:23]([CH3:32])[C:24]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[C:20]([C:14]3[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=3[Cl:12])[N:21]=2)=[O:34])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 166581-AminopiperidineHCID 10179718HCID 10179718, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 10205057HCID 10205057, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.33 mL (3.05 mmol) of 1-aminopiperidine in 2 mL of dry toluene under N2, 1.5 mL (3.05 mmol) of 2M trimethylaluminum in hexane was added with cooling in ice bath. The cold bath was removed, reaction was stirred for 1 h and 0.5 g (1.22 mmol) of ethyl 4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-1-methylimidazole-2-carboxylate in 3 mL of toluene, and 1.5 mL of CH2Cl2 was added. The mixture was heated in a 60° C. bath for 2 h, cooled, quenched with water and the pH was adjusted to 5 with 1.2 N HCl. The solution was extracted with EtOAc twice. The combined EtOAc layer was washed with brine, dried and concentrated. The residue was purified by flash chromatography using 30% EtOAc/hexane as an eluant to isolate the title compound. 1H NMR (500 MHz, CDCl3): δ 1.47 (m, 2H), 1.77–1.82 (m, 4H), 2.89 (s, 4H), 4.00 (s, 3H), 7.11–7.14 (m, 2H), 7.23–7.26 (m, 1H), 7.28–7.30 (m, 1H), 7.36–7.39 (m, 3H), 8.15 (s, 1H). LC-MS: Rt=3.6 min. m/e=465.1 (M+1).

Workup

  1. temperaturewith cooling in ice bath
  2. customThe cold bath was removed
  3. customreaction
  4. temperaturecooled
  5. customquenched with water
  6. extractionThe solution was extracted with EtOAc twice
  7. washThe combined EtOAc layer was washed with brine
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-20896ae7254648f0b8972c81cd631f09
Source dataset
uspto-grants-2006_06
Patent number
US07057051B2

Reaction notes

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