Methane → Ethyl 4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

HRID 2417794Notes

Reaction equation

HRID 2417794 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[NH2:20])[CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].N[C:22](N)=[O:23].C>C1(C)C=CC=CC=1>[C:1]([N:6]1[CH2:7][CH2:8][CH:9]([N:12]2[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[NH:20][C:22]2=[O:23])[CH2:10][CH2:11]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 297MethaneHCID 1176UreaHCID 104609Ethyl 4-[(2-amino-4-chlorophenyl)amino]piperidine-1-carboxylate

Product 1

HCID 104610Ethyl 4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 24.7 g of 1-carbethoxy-4-(2-amino-4-chloroanilino)-piperidine and 7.2 g of urea was heated to 160°-180° C. for 3.5 hours. The melt was taken up in 250 ml of toluene and heated, while stirring, until everything had dissolved. The solution was clarified with active charcoal, filtered and concentrated to 50 ml. The product was precipitated with diisopropyl ether. Melting point: 160° C.

Workup

  1. temperaturewas heated to 160°-180° C. for 3.5 hours
  2. temperatureheated
  3. dissolutionhad dissolved
  4. filtrationfiltered
  5. concentrationconcentrated to 50 ml
  6. customThe product was precipitated with diisopropyl ether

Sources & evidence

ORD record
ord-ce47b2e418934eda94a0f219f6f3ac23
Source dataset
uspto-grants-1984_09
Patent number
US04470989

Reaction notes

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