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Sodium Sulfate → 1-{4-[4-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}methaneamine

HRID 1850492
Notes
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Reaction equation

HRID 1850492 reaction equation
[CH3:1][C:2]1([CH3:28])[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.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:28])[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]([CH2:23][NH2:24])=[CH:25][CH:26]=4)[CH2:15][CH2:14]3)[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 594851044-[4-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]benzonitrile

Product 1

HCID 594850611-{4-[4-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}methaneamineYield 66%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To the THF (5.0 mL) solution of 4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]benzonitrile (180 mg, 0.479 mmol) synthesized in Example 90, lithium aluminum hydride (91 mg, 2.39 mmol) was slowly added under ice cooling, followed by stirring for 1.5 hours. To the reaction solution, sodium sulfate.10 hydrate (500 mg) was added. The temperature was raised to room temperature and the mixture was stirred for 16 hours. Undissolved residues were removed by filtration and the filtrate was concentrated under reduced pressure. To the resulting residue, hexane was added. The resulting solids were filtered to obtain the title compound 120 mg (yield 66%). Melting point was 156 to 158° C. (hexane-THF).

Workup

  1. stirringthe mixture was stirred for 16 hours
  2. customUndissolved residues were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the resulting residue, hexane was added
  5. filtrationThe resulting solids were filtered

Sources & evidence

ORD record
ord-2b793ba482fb47c5be63ff47060443c7
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957069B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes