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

HRID 743824Notes

Reaction equation

HRID 743824 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, 6.3; 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-52c2df281bed4a76a192cf048b946823
Source dataset
uspto-grants-1996_09
Patent number
US05556977

Reaction notes

Loading…