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 2173175Notes

Reaction equation

HRID 2173175 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 pumped 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): 275.38 [M+1]+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompumped over high vacuum pump overnight

Sources & evidence

ORD record
ord-6afc444ecdf148a385fd16ab0d2af258
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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