Hydrochloric Acid → HCID 20186857, compound

HRID 2309114Notes

Reaction equation

HRID 2309114 reaction equation
[Cl:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:18]=[C:19]([CH:40]=[CH:41][CH:42]=3)[O:20][C:21]3[N:25]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)[N:24]=[N:23][C:22]=3[C:35]([O:37]CC)=[O:36])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:18]=[C:19]([CH:40]=[CH:41][CH:42]=3)[O:20][C:21]3[N:25]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)[N:24]=[N:23][C:22]=3[C:35]([OH:37])=[O:36])[CH2:11][CH2:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20186856HCID 20186856, compound

Product 1

HCID 20186857HCID 20186857, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent2×

Procedure

Ethyl 5-{3-{3-[4-(4-chlorobenzyl)-1-piperazinyl]propoxy}phenoxy}-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylate, (8.00 g, 0.013 mole) was dissolved in ethanol, (150 ml) and water (50 ml) and sodium hydroxide (0.520 g, 0.013 mole) dissolved in water (5 ml) was added. The solution was stirred at room temperature for 5 hours. The reaction was neutralized with dilute hydrochloric acid and excess ethanol evaporated in vacuo. The aqueous solution was extracted with EtOAc, (three times), then chloroform (three times), and the organic extracts combined, dried (MgSO4), and evaporated in vacuo to a pale yellow foam. Trituration with diethyl ether gave a white solid which was filtered off and dried in vacuo to yield 92% of the title compound, mp (EtOH) 100°-2° C. (dec). νmax (mull) 1515, 1590, 1615, 3390 cm-1 δ(DMSOd6) 1.81 (2H, m, CH2), 2.50 (10H, m, piperazinyl+ CH2), 3.45 (2H, s, CH2N--) 3.70 (3H, s, OCH3), 3.89 (2H, t, J 6 Hz, OCH2), 4.75 (1H, bs, OH, exchangeable D2O), 5.35 (2H, s, N--CH2), 6.40 (2H, m, aromatics), 6.67 (1H, dd, J2, 8 Hz, aromatic), 7.00 (4H, ABq, Δν 84 Hz, J 9 Hz, C6H4OCH3), 7.19 (1H, t, J 8 Hz, aromatic) 7.32 (4H, ABq, Δν 17 Hz, J 8.5 Hz, --C6H4 --Cl). Mass spec. Observed mass 547.2342, theoretical mass 547.2350 (C31H34ClN5O5 --CO2).

Workup

  1. additionwas added
  2. customevaporated in vacuo
  3. extractionThe aqueous solution was extracted with EtOAc, (three times),
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo to a pale yellow foam
  6. customTrituration with diethyl ether gave a white solid which
  7. filtrationwas filtered off
  8. customdried in vacuo

Sources & evidence

ORD record
ord-f06a41883511413396cda77acef93998
Source dataset
uspto-grants-1987_09
Patent number
US04692526

Reaction notes

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