Piperidine → HCID 14390331, compound

HRID 623051Notes

Reaction equation

HRID 623051 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]([CH2:18][C:19]([OH:21])=O)[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:17]([CH2:18][C:19](=[O:21])[N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 682631,1'-CarbonyldiimidazoleHCID 15617195HCID 15617195, compound

Product 1

HCID 14390331HCID 14390331, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen bubbling, a mixture of 2-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.2 g, 0.015 mole) and 1,1'-carbonyldiimidazole (2.43 g, 0.015 mole) in 120 ml of tetrahydrofuran was stirred at room temperature for 3 hrs. Then, under nitrogen atmosphere, piperidine (1.92 g, 0.022 mole) was added and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was filtered and the filtrate was evaporated to dryness, then placed under high vacuum for 3-4 hrs. The residue was treated with water and the solid was collected by filtration, washed with water, and dried under high vacuum at 50°-60° C. overnight. The solid was recrystallized from isopropyl alcohol with refrigeration overnight. The solid was collected by filtration, washed with cold isopropyl alcohol and water, and dried under high vacuum at 50°-60° C. overnight to give 3.21 g (62%) of title compound, mp 153°-55° C.

Workup

  1. stirringto stir at room temperature overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. waitplaced under high vacuum for 3-4 hrs
  5. additionThe residue was treated with water
  6. filtrationthe solid was collected by filtration
  7. washwashed with water
  8. customdried under high vacuum at 50°-60° C. overnight
  9. customThe solid was recrystallized from isopropyl alcohol with refrigeration overnight
  10. filtrationThe solid was collected by filtration
  11. washwashed with cold isopropyl alcohol and water
  12. customdried under high vacuum at 50°-60° C. overnight

Sources & evidence

ORD record
ord-890ad390097d425a8825235fbe25c47b
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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