Propylamine → HCID 19043203, compound

HRID 467075Notes

Reaction equation

HRID 467075 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([CH3:12])[C:9](=O)[CH2:8][CH2:7]2.S([O-])([O-])(=O)=O.[Mg+2].[CH2:20]([NH2:23])[CH2:21][CH3:22]>ClCCl>[CH3:12][CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[Br:1])[CH2:7][CH2:8][C:9]1=[N:23][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 19043184HCID 19043184, compound

Product 1

HCID 19043203HCID 19043203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-bromo-1-methyl-2-tetralone (4.05 gm, 16.9 mMol) in dichloromethane (60 mL) were added magnesium sulfate (3.0 gm, 25 mMol) and n-propylamine (2.0 mL, 24.4 mMol). The mixture was stirred at room temperature for twenty hours. The reaction mixture was filtered through a bed of celite and the filtrate concentrated in vacuo to give 1-methyl-2-n-propylimino-8-bromo-1,2,3,4-tetrahydronaphthalene as a dark residue. p NMR (CDCl3): 7.56-7.24(m, 1H), 7.20-6.80(m, 2H), 4.20-3.88(q, J=7.2 Hz, 1H), 3.56-2.0(m, 6H), 1.88-1.52(sextet, J=5.4 Hz, 2H), 1.44-1.32(d, J=7.2 Hz), 3H), 1.16-0.84(t, J=5.4 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a bed of celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-4268fda2c63b4c169285f483b8557807
Source dataset
uspto-grants-1992_10
Patent number
US05158956

Reaction notes

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