Ammonia → 4-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxyacetamide

HRID 864828Notes

Reaction equation

HRID 864828 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([C:16]3[CH:27]=[CH:26][C:19]([O:20][CH2:21][C:22]([O:24]C)=O)=[CH:18][CH:17]=3)=[O:15])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[NH3:28]>CO>[N:1]1[CH:2]=[CH:3][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:13][C:14]([C:16]3[CH:27]=[CH:26][C:19]([O:20][CH2:21][C:22]([NH2:28])=[O:24])=[CH:18][CH:17]=3)=[O:15])[CH2:11][CH2:12]2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22118604Methyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxyacetate

Product 1

HCID 189184024-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxyacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product of Example 1 (200 mg) in methanol (10 ml), prepared under argon, was cooled to 4° C. and saturated with dry ammonia gas, then sealed in a pressure bottle and kept for 2 days. The orange crystals which formed, after filtration and washing with a little methanol, gave the title compound, 140 mg: m.p. 247° to 248° C.; NMR (d6DMSO) δ8.16 (2H, d), 7.99 (2H, d), 7.55 (1H, bs), 7.37 (1H, bs), 7.02 (2H, d), 6.81 (2H, d), 4.54 (2H, s), 3.85 (2H, s), 3.33 (4H, t), 2.60 (4H, t); m/e 355 (M+H)+ ; calculated for C19H22N4O3 : C, 64.4; H, 6.31 N, 15.8. found: C, 64.4; H, 6.4; N, 15.6%.

Workup

  1. customsealed in a pressure bottle
  2. customThe orange crystals which formed
  3. filtrationafter filtration
  4. washwashing with a little methanol

Sources & evidence

ORD record
ord-14d474c550354c7d9c9789a7e4bea41d
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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