Hydrogen Bromide → N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6,7-dihydroxy-1-methylisoquinoline dihydrobromide

HRID 35244Notes

Reaction equation

HRID 35244 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][C:14]([O:22]C)=[C:15]([O:20]C)[CH:16]=3)[CH:11]2[CH3:24])=[CH:6][CH:5]=1.[BrH:27]>>[BrH:27].[BrH:27].[NH2:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][C:14]([OH:22])=[C:15]([OH:20])[CH:16]=3)[CH:11]2[CH3:24])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 3033629Veradoline Hydrochloride

Product 1

HCID 14230315N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6,7-dihydroxy-1-methylisoquinoline dihydrobromide

Procedure

N-(4-Aminophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline dihydrochloride (10.0 g, 0.025 m) was dissolved in 49% HBr (25 ml) maintained under nitrogen and heated to 120° for 18 hr. after which time a white solid had precipitated. The mixture was cooled and the solid slurried with isopropanol (50 ml), stirred for 1 hr., and the solid collected by filtration. The solid was washed three times with isopropanol and vacuum dried at 100° for 48 hr. to give 8.5 g N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6,7-dihydroxy-1-methylisoquinoline dihydrobromide as an off-white solid, m.p. 275°-278°.

Workup

  1. temperaturemaintained under nitrogen
  2. temperatureheated to 120° for 18 hr
  3. customafter which time a white solid had precipitated
  4. temperatureThe mixture was cooled
  5. filtration, and the solid collected by filtration
  6. washThe solid was washed three times with isopropanol and vacuum
  7. customdried at 100° for 48 hr

Sources & evidence

ORD record
ord-927e402d66544e428ea75208f97b14a0
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Reaction notes

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