Hydrochloric Acid → 5-(4-Methyl-piperazin-1-yl)-2,3-dihydro-1H-isoindole dihydrochloride

HRID 424122Notes

Reaction equation

HRID 424122 reaction equation
C(OC([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[CH:14]=2)[CH2:9]1)=O)(C)(C)C.[ClH:24].O1CCOCC1>>[ClH:24].[ClH:24].[CH3:23][N:20]1[CH2:21][CH2:22][N:17]([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH2:9][NH:8][CH2:16]3)[CH2:18][CH2:19]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 592631315-(4-Methyl-piperazin-1-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

Product 1

HCID 666722875-(4-Methyl-piperazin-1-yl)-2,3-dihydro-1H-isoindole dihydrochloride

Procedure

5-(4-Methyl-piperazin-1-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (247 mg, 0.78 mmol) was treated with 4M HCl in dioxane (4 mL, 4 mmol) for 24 hours. Concentration in vacuo afforded the title compound quantitatively, which was used directly in the coupling reaction. 1H NMR (DMSO-d6) 11.13 (1H, br.s), 9.99 (2H, br.s), 7.27 (1H, d), 7.02-7.00 (2H, m), 4.43-4.37 (4H, m), 3.82-3.75 (2H, m), 3.49-3.43 (2H, m), 3.15-3.10 (4H, m), 2.79-2.78 (3H, s), 1.52 (9H, s). MS: [M+H]+ 218.

Workup

  1. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-2b6ffbf742ee47a9972bd58a9dbdcdc8
Source dataset
uspto-grants-2012_01
Patent number
US08101648B2

Reaction notes

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