Hydrogen Bromide → HCID 22853149, compound

HRID 1289058Notes

Reaction equation

HRID 1289058 reaction equation
Cl.[CH2:2]([NH:5][C@H:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:18]C)[C:12]=2[O:16]C)[CH2:7]1)[CH2:3][CH3:4].[BrH:20]>>[BrH:20].[CH2:2]([NH:5][C@H:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:18])[C:12]=2[OH:16])[CH2:7]1)[CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 22853153HCID 22853153, compound

Product 1

HCID 22853149HCID 22853149, compound

Conditions

Temperature
130 °C

Procedure

A solution of (S)-N-propyl-5,6-dimethoxy-1,2,3,4-tetrahydro-2-naphthylamine hydrochloride (22 g; 76.9 mmoles), prepared as described in example 2, in 48% hydrobromic acid (220 ml) was heated under reflux (about 130° C.) for 3 hours. The solvent was evaporated to dryness under vacuum and the residue was taken twice with toluene, by evaporating to dryness each time. The resultant crude was collected with ethyl acetate and filtered obtaining (S)-N-propyl-5,6-dihydroxy-1,2,3,4-tetrahydro-2-naphthylamine hydrobromide (23 g). m.p. 219°-222° C. [α]D =-54.59° (1% in methanol)

Workup

  1. temperaturewas heated
  2. customThe solvent was evaporated to dryness under vacuum
  3. customby evaporating to dryness each time
  4. customThe resultant crude was collected with ethyl acetate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4aa22fb0100f478c999671433e3b4c7d
Source dataset
uspto-grants-1998_05
Patent number
US05747513

Reaction notes

Loading…