Bromine → HCID 22041764, compound

HRID 1790300Notes

Reaction equation

HRID 1790300 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([CH2:14][CH:15]([NH2:17])[CH3:16])[CH:5]=1.[Br:18]Br>ClCCl>[ClH:1].[Br:18][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([O:3][CH3:2])=[CH:5][C:6]=1[CH2:14][CH:15]([NH2:17])[CH3:16]

Participants

4

Reactant 2

HCID 24408BromineHCID 22041750HCID 22041750, compound

Product 1

HCID 22041764HCID 22041764, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold heterogeneous solution (ice bath) of 2-(4-methoxy-naphthalen-2-yl) 1-methyl-ethylamine hydrochloride (0.10 g, 0.39 mmol, Example 11) in dichloromethane, was added bromine (0.07 g, 0.43 mmol) via syringe. After 1 h the volatiles were evaporated and the residue was partitioned in a mixture of ethyl acetate (20 mL) and a saturated aqueous solution of bicarbonate (20 mL). The organic layer was separated, dried (MgSO4), and concentrated in vacuo. The residue was dissolved in ethyl ether (20 mL) and the free amine was transformed to its correspondent hydrochloride salt by adding 1 M solution of hydrogen chloride in ethyl ether. The solid formed was collected by filtration (80 mg): 1H NMR (DMSO-d6) δ 1.21 (d, 3H, CH3), 3.24 (m, 2H), 3.60 (m, 11H), 3.66 (m, 1H), 4.02 (s, 3H, OCH3), 7.03 (s, 1H, Ar—H), 7.48–7.75 (m, 2H, Ar—H), 7.96 (m, 3H, NH3+), 8.17 (m, 2H, Ar—H); MS 296 (M+1).

Workup

  1. customAfter 1 h the volatiles were evaporated
  2. customthe residue was partitioned in a mixture of ethyl acetate (20 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in ethyl ether (20 mL)
  7. additionby adding 1 M solution of hydrogen chloride in ethyl ether
  8. customThe solid formed
  9. filtrationwas collected by filtration (80 mg)

Sources & evidence

ORD record
ord-b7b56b27075a459bb5c8651b01ad1115
Source dataset
uspto-grants-2006_07
Patent number
US07071225B2

Reaction notes

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