Ethyl 4-amino-1-piperidinecarboxylate → Ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-YL]amino]piperidine-1-carboxylate

HRID 1762817

Reaction equation

HRID 1762817 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl[C:14]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:17]2[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=2[N:15]=1>ClC(Cl)Cl>[F:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:18]2[C:17]3[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=3[N:15]=[C:14]2[NH:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 30202411-(4-Fluorobenzyl)-2-chlorobenzimidazole

Product 1

HCID 3019916Ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-YL]amino]piperidine-1-carboxylateYield 40.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 9.8 parts of ethyl 4-amino-1-piperidinecarboxylate and 15 parts of 2-chloro-1-(4-fluorophenylmethyl)-1H-benzimidazole was heated to 120° C. The mixture was stirred at 120° C. during 43 hours. After cooling, 100 parts of trichloromethane were added and the whole was thouroughly stirred. The mixture was washed with water. The aqueous layer was separated and the organic mixture was filtered and evaporated. The collected solid material was dissolved in 100 parts of water and subsequently 100 parts of 20% sodium hydroxide solution were added. The precipitate was filtered and dried in vacuo at 50° C., yielding 12.1 parts (40.5%) of ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate; mp. 181° C. (compound 21).

Workup

  1. temperatureAfter cooling
  2. stirringthe whole was thouroughly stirred
  3. washThe mixture was washed with water
  4. customThe aqueous layer was separated
  5. filtrationthe organic mixture was filtered
  6. customevaporated
  7. dissolutionThe collected solid material was dissolved in 100 parts of water and subsequently 100 parts of 20% sodium hydroxide solution
  8. additionwere added
  9. filtrationThe precipitate was filtered
  10. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-4cf92ec6199f4e86980cc57881e512a1
Source dataset
uspto-grants-1989_05
Patent number
US04835161

Linked notes

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