Hydrogen Bromide → HCID 19099734, compound

HRID 2352316Notes

Reaction equation

HRID 2352316 reaction equation
Cl.CO[C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C@H:8](N(CCC)CCC)[C@@H:9]2C.[BrH:22]>>[BrH:22].[CH2:9]1[C:10]2[C:5](=[CH:4][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 13487103HCID 13487103, compound

Product 1

HCID 19099734HCID 19099734, compound

Procedure

cis-5-Methoxy-1-methyl-2-(di-n-propylamino)tetralin hydrochloride (150 mg, 0.48 mmol) was heated in 48% aqueous HBr for 2 h at 120° C. under N2. The volatiles were evaporated in vacuo and the residue was applied to pre-coated PLC plates (silica gel 60 F254, Merck) which were eluted with CHCl3 -MeOH (9:1). After elution of the product the volatiles were evaporated in vacuo and the residue was recrystallized at least twice. giving cis-hydroxy-1-methyl-2-(di-n-propyl-amino)tetralin.Hbr (66 mg, 48%) of an isomeric purity >95% (GC, 225° C.) IR (KBr) ν3136 cm-1 (O-Hstr); NMR (MeOH-d4), δ1.05 (t,6H), δ1.31 (d,3H), δ1.50-3.74 (m,14H), δ6.44-6.69 (m,2H), δ6.81-7.07 (m,1H); MS (70 eV) m/z 261 (36%), 232 (100%), 161 (82%).

Workup

  1. customThe volatiles were evaporated in vacuo
  2. washwere eluted with CHCl3 -MeOH (9:1)
  3. washAfter elution of the product the volatiles
  4. customwere evaporated in vacuo
  5. customthe residue was recrystallized at least twice
  6. customHbr (66 mg, 48%) of an isomeric purity >95% (GC, 225° C.) IR (KBr) ν3136 cm-1 (O-Hstr)

Sources & evidence

ORD record
ord-ddaffb50dd034d53a307be0954cf9ee5
Source dataset
uspto-grants-1989_10
Patent number
US04876284

Reaction notes

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