Hydrogen Bromide → HCID 22850481, compound

HRID 2352317Notes

Reaction equation

HRID 2352317 reaction equation
Cl.C[O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C@H:10]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[C@@H:11]2[CH3:14])=[CH:6][CH:5]=1.O.CO.C(OCC)C.[BrH:30]>>[BrH:30].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C@H:10]([N:15]([CH2:16][CH2:17][CH3:18])[CH2:19][CH2:20][CH3:21])[C@@H:11]2[CH3:14])=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 13900424HCID 13900424, compoundHCID 21864698Diethyl ether methanol

Product 1

HCID 22850481HCID 22850481, compoundYield 84%

Procedure

cis-7-Methoxy-1-methyl-2-(di-n-propylamino) tetralin hydrochloride (500 mg, 1.60 mmol) was heated in 48% aqueous HBr (5ml) for 3 h at 140° C. under N2. Water (20 ml) was added and the volatiles were evaporated in vacuo. The faint orange-coloured residue was treated with abs. ethanol twice (with intervening evaporation). The dry residue was dissolved in methanol and the solution was treated with active charcoal. After filtration the solvent was evaporated, whereupon the residue was dissolved in methanol and ethyl ether was added. The obtained white crystals were recrystallized from MeOH-ethyl ether yielding the desired product (450 mg, 84% yield), m.p. 195°-196° C.

Workup

  1. customthe volatiles were evaporated in vacuo
  2. additionThe faint orange-coloured residue was treated with abs
  3. customethanol twice (with intervening evaporation)
  4. dissolutionThe dry residue was dissolved in methanol
  5. additionthe solution was treated with active charcoal
  6. filtrationAfter filtration the solvent
  7. customwas evaporated, whereupon the residue
  8. dissolutionwas dissolved in methanol
  9. additionethyl ether was added

Sources & evidence

ORD record
ord-56389f53c0dc400197f4b3420a334106
Source dataset
uspto-grants-1989_10
Patent number
US04876284

Reaction notes

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