Hydrogen Bromide → HCID 67822483, compound

HRID 1975412Notes

Reaction equation

HRID 1975412 reaction equation
[ClH:1].C[O:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C@H:8]([N:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18])[C@@H:9]2[CH3:14].Br>>[ClH:1].[OH:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C@H:8]([N:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18])[C@@H:9]2[CH3:14]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 67822470HCID 67822470, compound

Product 1

HCID 67822483HCID 67822483, compound

Procedure

cis-5-Methoxy-1-methyl-2-(N-n-pentyl-N-n-propyl-amino) tetralin hydrochloride (500 mg; 1.5 mmol) was heated in aqueous 48% HBr (3 ml) for 2 hours at 120° C. under N2. The mixture was evaporated and the residue was made alkaline with diluted NaHCO3 and extracted 3 times with ether. After drying (Na2SO4) and evaporation the product was precipitated as hydrochloride salt. Yield: 290 mg (60%) NMR (CDCl3). δ0.86 (t, 6H) δ1.17 (d, 3H), δ3.23-0.60 (m, 27H) δ5.36 (s, 1H phenolic) δ6.90 (m, 3H),MS (70 eV) m/z 289 (33%), 161 (100%), 232 (82%).

Workup

  1. customThe mixture was evaporated
  2. extractionextracted 3 times with ether
  3. customAfter drying
  4. custom(Na2SO4) and evaporation the product
  5. customwas precipitated as hydrochloride salt

Sources & evidence

ORD record
ord-b1290ebdbdf04345a384ab7158ce7e91
Source dataset
uspto-grants-1994_02
Patent number
US05286747

Reaction notes

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