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 1186963Notes

Reaction equation

HRID 1186963 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 it's freebase by partitioning between an organic solvent and saturated NaHCO3 solution. LC-MS (IE, m/z): 275.38 [M+1]−; tR=0.38 min.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-825b52a3ef344f798f2f0a6fd60852ed
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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