6-Benzenesulfonyl-naphthalene-1-carbonitrile → C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine

HRID 1715053Notes

Reaction equation

HRID 1715053 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20]#[N:21])=[CH:15][CH:14]=[CH:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([CH2:20][NH2:21])=[CH:15][CH:14]=[CH:13]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 590287716-Benzenesulfonyl-naphthalene-1-carbonitrile

Product 1

HCID 59028770C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Benzenesulfonyl-naphthalene-1-carbonitrile is dissolved in dry THF and cooled to ice bath temperature. Borane-THF complex is added and the reaction mixture is stirred under nitrogen overnight at room temperature. The reaction is quenched by addition of HCl and methanol, and made basic by addition of 1M NaOH. The resulting residue is extracted with EtOAc, and the organic layer is dried (MgSO4), filtered and concentrated under reduced pressure. The residue is recrystallized from HCl/EtOH to give C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine as a hydrochloride salt.

Workup

  1. temperaturecooled to ice bath temperature
  2. additionBorane-THF complex is added
  3. customThe reaction is quenched by addition of HCl and methanol
  4. additionmade basic by addition of 1M NaOH
  5. extractionThe resulting residue is extracted with EtOAc
  6. dry with materialthe organic layer is dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is recrystallized from HCl/EtOH

Sources & evidence

ORD record
ord-fc816dea732646988ea75ed94cbc0716
Source dataset
uspto-grants-2010_09
Patent number
US07799797B2

Reaction notes

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