2-Methoxyethylamine → 2-[4-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxy]-N-(2-methoxyethyl)acetamide

HRID 2222

Reaction equation

HRID 2222 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](OC)=[O:23])=[CH:18][CH:17]=3)=[O:15])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[CH3:28][O:29][CH2:30][CH2:31][NH2:32]>>[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]([NH:32][CH2:31][CH2:30][O:29][CH3:28])=[O:23])=[CH:18][CH:17]=3)=[O:15])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 22118604Methyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxyacetate

Product 1

HCID 189183842-[4-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxy]-N-(2-methoxyethyl)acetamide

Procedure

A suspension of the product of Example 1, (100 mg) in 2-methoxyethylamine (1 ml) was stirred for 18 hours. Filtration of the solid and washing with ethyl acetate gave the title compound, 70 mg, as a white crystalline solid: m.p. 142°-145° C.; NMR (d6DMSO+d4 acetic acid) δ 8.20 (2H, d), 8.00 (2H, d), 7.14 (2H, d), 7.06 (2H, d), 4.62 (2H, s), 3.72 (4H, t), 3.38 (4H, m), 3.26 (3H, s), 2.78 (4H, t); m/e 413 (M+H)+ ; calculated for C22H28N4O4 : C, 64.1; H, 6.8; N, 13.6. found: C, 63.9; H, 6.8; N, 13.3%.

Workup

  1. filtrationFiltration of the solid
  2. washwashing with ethyl acetate

Sources & evidence

ORD record
ord-446b034cd2a240b1811399997a196a51
Source dataset
uspto-grants-1998_03
Patent number
US05728701

Linked notes

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