Piperidine → HCID 14390334, compound

HRID 2351715Notes

Reaction equation

HRID 2351715 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18](=[O:20])[N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 682631,1'-CarbonyldiimidazoleHCID 14390205HCID 14390205, compound

Product 1

HCID 14390334HCID 14390334, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen bubbling, a mixture of 2-(3-bromophenyl)-3H-imidazo [4,5-b]pyridine-3-acetic acid (4.98 g, 0.015 mole) and 1,1'-carbonyldiimidazole (2.59 g, 0.016 mole) in 120 ml of tetrahydrofuran was stirred at room temperature for 4 hrs. The piperidine (2.55 g, 0.03 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 hrs. The solid was treated with water, collected by filtration, washed with water, and dried at 50° C. under high vacuum over the weekend to give 3.93 g (66%) of title compound, mp 157°-58° 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 hrs
  5. additionThe solid was treated with water
  6. filtrationcollected by filtration
  7. washwashed with water
  8. customdried at 50° C. under high vacuum over the weekend

Sources & evidence

ORD record
ord-f5370487302b4524b92f99f59d2201a2
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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