Sodium hydride → HCID 20186856, compound

HRID 2309113Notes

Reaction equation

HRID 2309113 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][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:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:29]1[N:33]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)[N:32]=[N:31][C:30]=1[C:43]([O:45][CH2:46][CH3:47])=[O:44]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][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:20]=[CH:21][CH:22]=3)[O:23][C:29]3[N:33]([CH2:34][C:35]4[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=4)[N:32]=[N:31][C:30]=3[C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:9][CH2:8]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12937508HCID 12937508, compoundHCID 20186859HCID 20186859, compound

Product 1

HCID 20186856HCID 20186856, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[4-(4-chlorobenzyl)piperazin-1-yl]-3-(3-hydroxyphenoxy)propane (7.00 g, 0.019 mole), in dry dimethyl formamide, (200 ml) was treated portionwise with 60% sodium hydride in oil, (0.776 g, 0.019 mole), under a slow stream of nitrogen. The mixture was stirred at room temperature for 0.5 h, then Ethyl 5-chloro-1-(4-methoxybenzyl)-1,2,3-triazole 4-carboxylate (5.74 g, 0.019 mole) was added. The reaction was stirred at 100° C. for 24 hours, then cooled and the solvent removed in vacuo. The brown residue was partitioned between ethyl acetate and water and the organic phase separated, washed with water (twice), and dried, (MgSO4). Evaporation in vacuo gave the crude product as a pale brown oil which was purified by column chromatography to yield 8.52 g (72%) of the title compound as a pale yellow oil. νmax (film) 1510, 1560, 1590, 1615, 1730, 2810, 2940 cm-1 δ(CDCl3 ) 1.11 (3H, t, J 7 Hz, ester CH3), 1.91 (2H, m, CH2), 2.51 (10H, piperazinyl+CH2), 3.46 (2H, s, --NCH2), 3.73 (3H, s, OCH3), 3.87 (2H, t, J 6 Hz, OCH2), 4.18 (2H, q, J 7 Hz, ester CH2), 5.33 (2H, s, --NCH2), 6.33 (2H, m, aromatics), 6.80 (1H, m, aromatics), 7.00 (4H, ABq, Δν=39 Hz, J 9 Hz, --C6H4OCH3), 7.16 (1H, m, aromatics), 7.28 (4H, s, C6H4 --Cl). Mass Spec. Observed mass 619.2572, theoretical mass 619.2561 (C33H38ClN5O5).

Workup

  1. stirringThe reaction was stirred at 100° C. for 24 hours
  2. temperaturecooled
  3. customthe solvent removed in vacuo
  4. customThe brown residue was partitioned between ethyl acetate and water
  5. customthe organic phase separated
  6. washwashed with water (twice), and
  7. customdried
  8. customEvaporation in vacuo
  9. customgave the crude product as a pale brown oil which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-40dbac5a890f4f11a99cc1b3cabae962
Source dataset
uspto-grants-1987_09
Patent number
US04692526

Reaction notes

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