Dichloromethane → 7-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-ylmethanamine

HRID 510541Notes

Reaction equation

HRID 510541 reaction equation
[N:1]1([CH:5]2[CH:14]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]3[CH:12]=[C:11]([C:22]#[N:23])[CH:10]=[CH:9][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.ClCCl>CO.[Ni]>[N:1]1([CH:5]2[CH:14]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:13]3[CH:12]=[C:11]([CH2:22][NH2:23])[CH:10]=[CH:9][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 574714047-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 595477987-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-ylmethanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

7-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (340 mg, 1.12 mmol) was dissolved in dry methanol (20 mL) under a nitrogen atmosphere. Raney nickel (900 mg, 3.36 mmol) was added under nitrogen and the reaction mixture stirred at room temperature for 48 h under an atmosphere of hydrogen. Methanol (20 mL) and dichloromethane (30 mL) were added. After stirring at room temperature for 20 minutes the catalyst was removed by filtration and the solvent evaporated in vacuo. Yield: 338 mg (1.10 mmol, 98%).

Workup

  1. stirringAfter stirring at room temperature for 20 minutes the catalyst
  2. customwas removed by filtration
  3. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-21d7af3161e747789abebf819ba4f61d
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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