Water → 4-[4-(2,4,6,7-Tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]benzamide

HRID 1850438Notes

Reaction equation

HRID 1850438 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[C:7]([CH3:27])=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=4)[CH2:15][CH2:14]3)[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1.[OH-:28].[K+].O>C(O)(C)(C)C>[CH3:1][CH:2]1[CH2:6][C:5]2[C:7]([CH3:27])=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:20]=[CH:21][C:22]([C:23]([NH2:24])=[O:28])=[CH:25][CH:26]=4)[CH2:15][CH2:14]3)[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 594850044-[4-(2,4,6,7-Tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]benzonitrile

Product 1

HCID 594850504-[4-(2,4,6,7-Tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]benzamideYield 48%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

The mixture of 4-[4-(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]benzonitrile (70 mg, 0.194 mmol) synthesized in Reference example 29 and potassium hydroxide (33 mg, 0.582 mmol) was stirred in tert-butanol (2.0 mL) at 80° C. for 20 hours. After adding water, solids obtained were filtered and washed with ethanol to obtain the title compound 35 mg (yield 48%). Melting point was 240 to 245° C. (ethanol).

Workup

  1. customobtained
  2. filtrationwere filtered
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-c4fe1636128c4397a5abb5fa57b2a7b7
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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