4-Amino-1,2,2,6,6-pentamethylpiperidine → 4-(5,6-Dichlorobenzimidazol-2-yl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-3-methoxybenzamide

HRID 1352665Notes

Reaction equation

HRID 1352665 reaction equation
[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15](O)=[O:16])=[CH:11][C:10]=3[O:18][CH3:19])[NH:8][C:4]=2[CH:3]=1.Cl.CN(C)CCCN=C=NCC.[CH3:35][N:36]1[C:41]([CH3:43])([CH3:42])[CH2:40][CH:39]([NH2:44])[CH2:38][C:37]1([CH3:46])[CH3:45]>CN(C=O)C.C1COCC1.C1COCC1>[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([NH:44][CH:39]4[CH2:38][C:37]([CH3:45])([CH3:46])[N:36]([CH3:35])[C:41]([CH3:43])([CH3:42])[CH2:40]4)=[O:16])=[CH:11][C:10]=3[O:18][CH3:19])[NH:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 211011665,6-Dichloro-2-(4-carboxy-2-methoxyphenyl)benzimidazole

Product 1

HCID 99134174-(5,6-Dichlorobenzimidazol-2-yl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-3-methoxybenzamideYield 47.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A solution of 5,6-dichloro-2-(4-carboxy-2-methoxyphenyl)benzimidazole (0.8 g, 2,36 mmol), prepared as described in Preparation 6,1-hydroxybenzotriazole (0.32 g, 2.36 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.56 g, 2.9 mmol) in 80 ml of DMF/THF (50:50) was refluxed for 5 h. A solution of 1,2,2,6,6-pentamethyl-4-aminopiperidine (0.5 g, 2.9 mmol) in THF (5 ml) was added dropwise and the reaction was refluxed for additional 3 h. After cooling, solvent was removed under reduced pressure and the residue was treated with 1N NaOH (10 ml) and extracted with dichloromethane (50 ml). The organic layer was washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was triturated with diisopropyl ether (150 ml), stirred for 1 h, filtered to give 0.55 g of the title compound (yield 47.6%), mp=285–286° C.

Workup

  1. temperaturewas refluxed for 5 h
  2. temperaturethe reaction was refluxed for additional 3 h
  3. temperatureAfter cooling
  4. customsolvent was removed under reduced pressure
  5. additionthe residue was treated with 1N NaOH (10 ml)
  6. extractionextracted with dichloromethane (50 ml)
  7. washThe organic layer was washed with water
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. customThe residue was triturated with diisopropyl ether (150 ml)
  12. filtrationfiltered

Sources & evidence

ORD record
ord-af7ad8f0a1dc42b390a8d59218c54b8b
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

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