Allylamine → 7-(Allylamino)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466051Notes

Reaction equation

HRID 1466051 reaction equation
O=[C:2]1[CH2:11][C:10]2[CH:9]=[C:8]([C:12]#[N:13])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.BrC1C=C2C(CCC(=O)C2)=CC=1.[CH2:26]([NH2:29])[CH:27]=[CH2:28].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CC(O)=O>[CH2:26]([NH:29][CH:2]1[CH2:11][C:10]2[CH:9]=[C:8]([C:12]#[N:13])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1)[CH:27]=[CH2:28]

Participants

7

Reactant 4

HCID 7853AllylamineHCID 36915747-Bromo-2-tetraloneHCID 5049666Sodium triacetoxyborohydrideHCID 675155667-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 895248047-(Allylamino)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile [prepared from commercially available 7-bromo-2-tetralone following a similar procedure as described in WO2004/071389A2](500 mg, 2.9 mmol) in 20 mL of anhydrous DCM was added 3 drops of HOAc, allylamine (330 mg, 5.8 mmol) and NaBH(OAc)3 (2.46 g, 12 mmol), and the mixture was stirred at RT under nitrogen for 48 hours. DCM was added and the mixture was washed with saturated NaCO3 and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give 7-(Allylamino)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile.

Workup

  1. washthe mixture was washed with saturated NaCO3 and brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-197bc19827bd4ec7aa10e8903aa803b7
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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