N-(2-Aminoethyl)piperidine → HCID 14390296, compound

HRID 2351691Notes

Reaction equation

HRID 2351691 reaction equation
[Cl: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.[NH2:33][CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([NH:33][CH2:34][CH2:35][N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[O:20])[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 33944N-(2-Aminoethyl)piperidineHCID 682631,1'-CarbonyldiimidazoleHCID 143904542-(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390296HCID 14390296, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.4 g, 0.0188 mole), 1,1'-carbonyldiimidazole (3.0 g, 0.0188 mole) in anhydrous tetrahydrofuran (150 ml) was stirred at room temperature with a stream of nitrogen bubbling through it for 21/2 hours. The nitrogen flow was stopped and a solution of 1-(2-aminoethyl)piperdine (2.4 g, 0.0188 mole) in dry tetrahydrofuran (50 ml) was added. The solution was stirred at room temperature under nitrogen for 2 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between methylene chloride (75 ml) and water (75 ml). The layers were separated and the aqueous portion washed with methylene chloride (25 ml). The organic layers were combined and washed with potassium bicarbonate solution (2×50ml), water (25ml), dried over sodium sulfate, and concentrated in vacuo. The residue (6.6 g) was recrystallized from isopropyl alcohol-isopropyl ether to give 3.5 g (47%). Recrystallization from isopropyl alcohol-isopropyl ether gave 2.5 g of cream colored solid, mp 114°-115° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between methylene chloride (75 ml) and water (75 ml)
  3. customThe layers were separated
  4. washthe aqueous portion washed with methylene chloride (25 ml)
  5. washwashed with potassium bicarbonate solution (2×50ml), water (25ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue (6.6 g) was recrystallized from isopropyl alcohol-isopropyl ether
  9. customto give 3.5 g (47%)
  10. customRecrystallization from isopropyl alcohol-isopropyl ether
  11. customgave 2.5 g of cream

Sources & evidence

ORD record
ord-75f15ae62fae4c20a4ddceb8833ea9d1
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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