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

HRID 2173114Notes

Reaction equation

HRID 2173114 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[CH:14]=2)[CH2:8][CH2:7][N:6]1C([O-])=O)(C)C.[ClH:26]>O1CCOCC1>[ClH:26].[N:9]1([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[CH:14]=2)[CH2:10][CH2:5][NH:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866472981,1-Dimethylethyl-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate

Product 1

HCID 666467325-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To 1,1-dimethylethyl-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate (120 g, 347 mmol) in dioxane (800 mL) was added 4 N HCl in dioxane (87.0 mL, 347 mmol) and the resulting mixture was stirred at room temperature over night. The reaction mixture was concentrated and stored under vacuum overnight to afford 5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one hydrochloride. This can be used as is or converted to the free base by partitioning between an organic solvent and saturated NaHCO3 solution. MS: m/z 247 (M+1)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customstored under vacuum overnight

Sources & evidence

ORD record
ord-675ece841fae40a093ce360e904bc9e4
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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