1,3-Dibromopropane → 7-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1044523Notes

Reaction equation

[NH2:1][CH:2]1[CH:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[CH:9]=[C:8]([C:19]#[N:20])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.Br[CH2:22][CH2:23][CH2:24]Br.C(N(CC)CC)C>C(#N)C>[N:1]1([CH:2]2[CH:11]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:10]3[CH:9]=[C:8]([C:19]#[N:20])[CH:7]=[CH:6][C:5]=3[CH2:4][CH2:3]2)[CH2:24][CH2:23][CH2:22]1

Participants

Conditions

Temperature: 120 °C

Procedure

7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (790 mg, 3.03 mmol), 1,3-dibromopropane (0.4 mL, 3.93 mmol) and triethylamine (0.914 mL, 6.56 mmol) were dissolved in acetonitrile (8 mL) and the reaction mixture heated to 120° C. in the microwave for 2 h. The solvent was evaporated in vacuo. Water (30 mL) and ethyl acetate (40 mL) were added. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and the solvent evaporated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). Yield: 346 mg (1.14 mmol, 37.6%).

Workup

customThe solvent was evaporated in vacuo
additionWater (30 mL) and ethyl acetate (40 mL) were added
customThe layers were separated
extractionthe aqueous layer extracted with ethyl acetate
dry with materialThe combined organic extracts were dried (MgSO4)
customthe solvent evaporated in vacuo
customThe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)

Sources & evidence

ORD record: ord-8eae3ba9a4f647eb968cd773baa66ae4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563617B2

Reaction notes

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