Hydrogen Bromide → HCID 14848601, compound

HRID 1033953Notes

Reaction equation

HRID 1033953 reaction equation
Cl.[CH2:2]([NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:20]C)=[CH:15][CH:16]=2)[CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BrH:22]>C(O)(=O)C>[BrH:22].[CH2:2]([NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([OH:20])=[CH:15][CH:16]=2)[CH2:11]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen Bromide2×HCID 14750911HCID 14750911, compound

Product 1

HCID 14848601HCID 14848601, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-benzylamino-7-methoxytetralin hydrochloride (25 g) described in Preparation I step (a), and 33% hydrobromic acid in acetic acid (215 ml) in the presence of 48% hydrobromic acid (36 ml) is refluxed, under stirring, for 2 hours. The reaction mixture is then concentrated to dryness under reduced pressure and the residue is taken up in absolute ethanol (100 ml) and concentrated to dryness. The step of taking up in absolute ethanol and concentrating to dryness is repeated two other times and the thus obtained product is finally triturated with acetone (150 ml) and filtered yielding 2-benzylamino-7-hydroxytetralin hydrobromide (25.3 g). M.p. 198°-200° C. This product is then dissolved in hot water (1300 ml), the solution is cooled and concentrated ammonium hydroxide is then added thereto. The free base is extracted with ethyl acetate, the organic solution is dried and the solvent is evaporated off yielding a solid which is crystallized from toluene (250 ml). 2-Benzylamino-7-hydroxytetralin free base (14 g) is thus obtained . M.p. 161°-163° C.

Workup

  1. temperatureis refluxed
  2. concentrationThe reaction mixture is then concentrated to dryness under reduced pressure
  3. concentrationconcentrated to dryness
  4. concentrationconcentrating to dryness
  5. customthe thus obtained product is finally triturated with acetone (150 ml)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-10f6b8fe1922498ca4b56dc06de0c572
Source dataset
uspto-grants-1994_05
Patent number
US05312961

Reaction notes

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