Hydrochloric Acid → 4-methyl-5-[1-(methyloxy)-2-piperazin-1-ylethyl]-2-benzofuran-1(3H)-one hydrochloride

HRID 2173164Notes

Reaction equation

HRID 2173164 reaction equation
CC([CH:5]1[CH2:10][N:9]([CH2:11][CH:12]([C:15]2[CH:24]=[CH:23][C:18]3[C:19](=[O:22])[O:20][CH2:21][C:17]=3[C:16]=2[CH3:25])[O:13][CH3:14])[CH2:8][CH2:7][N:6]1C([O-])=O)(C)C.[ClH:29]>O1CCOCC1>[ClH:29].[CH3:25][C:16]1[C:17]2[CH2:21][O:20][C:19](=[O:22])[C:18]=2[CH:23]=[CH:24][C:15]=1[CH:12]([O:13][CH3:14])[CH2:11][N:9]1[CH2:10][CH2:5][NH:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866472941,1-Dimethylethyl-4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-(methyloxy)ethyl]-piperazine-1-carboxylate

Product 1

HCID 684302344-methyl-5-[1-(methyloxy)-2-piperazin-1-ylethyl]-2-benzofuran-1(3H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl-4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-(methyloxy) ethyl]-piperazine-1-carboxylate was treated with 4M HCl in dioxane (4 mL) and stirred at room temperature for 1 h. The reaction mixture was concentrated to dryness. Analysis by LC indicated complete removal of the Bac group and formation of compound 4-methyl-5-[1-(methyloxy)-2-piperazin-1-ylethyl]-2-benzofuran-1(3H)-one hydrochloride. 1H-NMR (DMSO, 500 MHz), δ 7.747 (d, J=7.5 Hz, 1H), 7.577 (d, J=7.5 Hz, 1H), 5.402-5.388 (m, 2H), 5.113 (d, J=9 Hz, 1H), 3.850 (s, 3H), 3.496-3.327 (m, 8H), 3.228-3.140 (m, 3H), 2.500 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customremoval of the Bac group and formation of compound 4-methyl-5-[1-(methyloxy)-2-piperazin-1-ylethyl]-2-benzofuran-1(3H)-one hydrochloride

Sources & evidence

ORD record
ord-53019e73bccb4726a6c0e3ae8c24af06
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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