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

HRID 1186932Notes

Reaction equation

HRID 1186932 reaction equation
CC([CH:5]1[CH2:10][N:9]([CH2:11][CH:12]([F:24])[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:28]>O1CCOCC1>[ClH:28].[F:24][CH:12]([C:13]1[CH:22]=[CH:21][C:16]2[C:17](=[O:20])[O:18][CH2:19][C:15]=2[C:14]=1[CH3:23])[CH2:11][N:9]1[CH2:10][CH2:5][NH:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866472931,1-Dimethylethyl-4-[2-fluoro-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate

Product 1

HCID 666467295-(1-fluoro-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl-4-[2-fluoro-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate (0.18 g) was treated with 4M HCl in dioxane (4 mL) and stirred at room temperature for 1 h. The mixture was then concentrated to dryness. Analysis by LC indicated complete removal of the Boc group and formation of compound 5-(1-fluoro-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one hydrochloride. 1H-NMR (DMSO, 500 MHz), δ 7.744 (d, J=7.5 Hz, 1H), 7.612 (d, J=7.5 Hz, 1H), 6.264-6.167 (m, 1H), 5.382 (s, 2H), 3.362-3.309 (m, 2H), 3.255-3.125 (m, 8H), 3.078-3.049 (m, 1H), 2.499 (s, 3H)

Workup

  1. concentrationThe mixture was then concentrated to dryness
  2. customremoval of the Boc group and formation of compound 5-(1-fluoro-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one hydrochloride

Sources & evidence

ORD record
ord-f064d7d40b7b487b9a7d82dfbb8fb756
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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