Phenylacetic Acid → 4-benzyloxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide

HRID 1177838Notes

Reaction equation

HRID 1177838 reaction equation
CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH2:32]([O:39][C:40]1[CH:57]=[CH:56][C:43]([C:44]([NH:46][CH2:47][C:48](=[O:55])[N:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)=[O:45])=[CH:42][CH:41]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[C:58]1([CH2:64][C:65](O)=[O:66])[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>O.CN(C=O)C>[CH2:32]([O:39][C:40]1[CH:57]=[CH:56][C:43]([C:44]([NH:46][CH2:47][C:48](=[O:55])[N:49]2[CH2:50][CH2:51][N:52]([C:65](=[O:66])[CH2:64][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH2:53][CH2:54]2)=[O:45])=[CH:42][CH:41]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

8

Reactant 5

HCID 999Phenylacetic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 595595894-benzyloxy-N-(2-oxo-2-piperazin-1-yl-ethyl)-benzamide

Product 1

HCID 251659104-benzyloxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamideYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDCI.HCl (122 mg, 0.634 mmol), HOBT (68 mg, 0.51 mmol) and DIPEA (220 μL, 1.27 mmol) were added to a mixture of 4-benzyloxy-N-(2-oxo-2-piperazin-1-yl-ethyl)-benzamide (150 mg, 0.42 mmol), DMF (5 mL) and phenyl acetic acid (69 mg, 0.51 mmol). The resulting mixture was allowed to stir at room temperature overnight. Water was then added, and the product was extracted using EtOAc. The organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford a crude product, which was purified twice by column chromatography (using silica gel with a mesh size of 60-120, and 80:20 EtOAc:hexane as the eluent) to afford 4-benzyloxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide in 55% yield. LC-MS purity: 92% 1H NMR (DMSO-D6): δ 8.4 (t, 1H), 7.8 (d, 2H), 7.4 (m, 7H), 7.2 (d, 3H), 7.1 (d, 2H), 5.2 (s, 2H), 4.1 (d, 2H), 3.8 (d, 2H), 3.5 (m, 8H).

Workup

  1. extractionthe product was extracted
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford a crude product, which
  6. customwas purified twice by column chromatography (

Sources & evidence

ORD record
ord-a764bb8425c14dd38a6f34f993ca2b00
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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