Hydrochloric Acid → HCID 69142710, compound

HRID 1794080Notes

Reaction equation

HRID 1794080 reaction equation
[ClH:1].O1CCOCC1.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:26]=2)=[O:22])[CH2:17][CH2:16]1)=O)(C)(C)C>CO.CCOCC>[ClH:1].[C:34]1([CH2:33][CH2:32][O:31][C:27]2[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=2)[CH2:24][O:23][C:21]([N:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)=[O:22])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69142501HCID 69142501, compound

Product 1

HCID 69142710HCID 69142710, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

4M HCl in 1,4-dioxane (2.3 mL, 9.2 mmol) was added to a solution of piperazine-1,4-dicarboxylic acid 3-(2-phenylethoxy)benzyl ester tert-butyl ester (0.10 g, 0.23 mmol) in methanol (2 mL) and ether (2 mL) and the solution was left to stand with occasional swirling at room temperature for 3 h. The solution was concentrated in vacuo and the residue was triturated with ether to yield the title compound (0.08 g, 93%) as a white solid. 1H-NMR (400 MHz, d6-DMSO): 3.03 (2H, t, J=6.8 Hz), 3.08 (4H, m), 3.61 (4H, m), 4.19 (2H, t, J=7.0 Hz), 5.06 (2H, s), 6.88–6.94 (3H, m), 7.20–7.33 (6H, m) and 9.19 (2H, br s).

Workup

  1. waitthe solution was left
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-8a10472660fe4288a8024189bc0f9bb3
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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