tert-Butyl-4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)propyl]piperazine-1-carboxylate → 4-Methyl-5-(1-methyl-2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one

HRID 1519497Notes

Reaction equation

HRID 1519497 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:17]2[CH:26]=[CH:25][C:20]3[C:21](=[O:24])[O:22][CH2:23][C:19]=3[C:18]=2[CH3:27])[CH3:16])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[CH3:27][C:18]1[C:19]2[CH2:23][O:22][C:21](=[O:24])[C:20]=2[CH:25]=[CH:26][C:17]=1[CH:15]([CH3:16])[CH2:14][N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 66643993tert-Butyl-4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)propyl]piperazine-1-carboxylate

Product 1

HCID 595686964-Methyl-5-(1-methyl-2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl-4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)propyl]piperazine-1-carboxylate (160 mg, 0.43 mmol) was stirred in TFA (3 mL) at r.t for 3 hr. The reaction was concentrated and pump over high vacuum pump overnight to give the desired product, which could be converted to its freebase by partitioning between an organic solvent and saturated NaHCO3 solution. LC-MS (IE, m/z): 275 [M+1]+.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-cc8bb9bf6e144a10a96fa43066adb880
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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