Methylamine → 2-[4-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxy]-N-methylacetamide

HRID 743825

Reaction equation

HRID 743825 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.[CH3:28][NH2:29]>C(O)C>[N:1]1[CH:6]=[CH:5][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]([NH:29][CH3:28])=[O:24])=[CH:18][CH:17]=3)=[O:15])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22118604Methyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxyacetate

Product 1

HCID 189185792-[4-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxy]-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of the product of Example 1 (100 mg) in a 33% w/v solution of methylamine in ethanol (3 ml) was stirred for 18 hours. The solid formed, after filtration and washing with a little ethyl acetate, gave the title compound, 65 mg: m.p. 169°-171° C.; NMR (d6DMSO) δ8.14 (2H, d), 8.06 (1H, bq), 8.00 (2H, d), 7.05 (2H, d), 6.80 (2H, d), 4.56 (2H, s), 3.82 (2H, s), 3.30 (4H, t), 2.66 (3H, d), 2.61 (4H, t); m/e 369 (M+H)+ ; calculated for C20H24N4O3 : C, 65.2; H, 6.6; N, 15.2. found: C, 65.0; H, 6.8; N, 15.1%.

Workup

  1. customThe solid formed
  2. filtrationafter filtration
  3. washwashing with a little ethyl acetate

Sources & evidence

ORD record
ord-5bd9048fda0e4996823e4784c4549d15
Source dataset
uspto-grants-1996_09
Patent number
US05556977

Linked notes

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