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

HRID 2173121Notes

Reaction equation

HRID 2173121 reaction equation
CC([CH:5]1[CH2:10][N:9]([CH2:11][CH2:12][C:13]2[CH:22]=[CH:21][C:16]3[C:17](=[O:20])[O:18][CH2:19][C:15]=3[C:14]=2[CH3:23])[CH2:8][CH2:7][N:6]1C([O-])=O)(C)C.[ClH:27]>O1CCOCC1>[ClH:27].[CH3:23][C:14]1[C:15]2[CH2:19][O:18][C:17](=[O:20])[C:16]=2[CH:21]=[CH:22][C:13]=1[CH2:12][CH2:11][N:9]1[CH2:10][CH2:5][NH:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866472991,1-Dimethylethyl-4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate

Product 1

HCID 675172294-methyl-5-(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)ethyl]piperazine-1-carboxylate (245 mg) was treated with 4N HCl in dioxane solution and the reaction was monitored until completion. The mixture was concentrated to afford 4-methyl-5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one hydrochloride. The hydrochloride can be converted to free base as needed by partitioning between organic solvent (EtOAc, DCM, or 30% IPA/CHCl3) and saturated Na2CO3 solution.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-0cf32b873cd344128155918e66c30387
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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