Tetrahydrofuran → HCID 13792188, compound

HRID 1899892Notes

Reaction equation

HRID 1899892 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([NH:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)=[C:4]([N+:20]([O-])=O)[CH:3]=1.[O:23]1CCC[CH2:24]1>[Pt].C(O)C>[CH3:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH:7]3[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]3)[C:24](=[O:23])[NH:20][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 13792164HCID 13792164, compound

Product 1

HCID 13792188HCID 13792188, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8.23 g of ethyl 4-(4-methyl-2-nitroanilino)-1-piperidinecarboxylate, 200 mL of tetrahydrofuran, 225 mL of ethanol and 2 g of 5% platinum on carbon was stirred under an atmosphere of hydrogen for 7 h. The catalyst was filtered off and the filtrate concentrated to to a thick oil. To an ice cold, vigorously stirred solution of the resulting crude ethyl 4-(4-methyl-2-aminoanilino)-1-piperidinecarboxylate in 500 mL of ethyl acetate was added 500 mL of saturated sodium carbonate followed by 20 mL of 1.9 M phosgene in toluene dropwise over 30 min. After stirring overnight at room temperature, the layers were separated and the organic layer dried over MgSO4 and concentrated to dryness. Trituration of the residue with ether-hexane gave 8 g of ethyl 4-(5-methyl-2-oxo-1-benzimidazolinyl)piperidine-1-carboxylate as a white crystalline solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated to to a thick oil
  3. additionTo an ice cold, vigorously stirred solution of the resulting crude ethyl 4-(4-methyl-2-aminoanilino)-1-piperidinecarboxylate in 500 mL of ethyl acetate was added 500 mL of saturated sodium carbonate
  4. waitfollowed by 20 mL of 1.9 M phosgene in toluene dropwise over 30 min
  5. stirringAfter stirring overnight at room temperature
  6. customthe layers were separated
  7. dry with materialthe organic layer dried over MgSO4
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2e097dd438704e418ef533f596ccd808
Source dataset
uspto-grants-1996_11
Patent number
US05574044

Reaction notes

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