Pyridine → 1-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-3-methyl-2-bromobutan-1-one

HRID 1760042Notes

Reaction equation

HRID 1760042 reaction equation
[Br:1][CH:2]([CH:6]([CH3:8])[CH3:7])[C:3](Cl)=[O:4].N1C=CC=CC=1.Cl.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH2:24][NH:23][CH2:22][CH2:21]2>CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl>[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH2:24][N:23]([C:3](=[O:4])[CH:2]([Br:1])[CH:6]([CH3:8])[CH3:7])[CH2:22][CH2:21]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 124869822-Bromo-3-methylbutanoyl chloride

Product 1

HCID 225999051-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-3-methyl-2-bromobutan-1-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

Racemic body α-bromoisovaleryl chloride (327 mg, 1.64 mmol) on the market and 4-(N,N-dimethylamino)pyridine (about 10 mg) were added to a pyridine (8 ml) suspension of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (472 mg, 2.05 mmol), and the mixture was stirred at room temperature for 3 hours. The reaction solution was diluted with chloroform (50 ml), washed with 1 N hydrochloric acid (50 ml) and a 1 N aqueous sodium hydroxide solution (50 ml), dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and used, without isolating and purifying the obtained gummy substance, in the reactions in Examples 27 and 28.

Workup

  1. washwashed with 1 N hydrochloric acid (50 ml)
  2. dry with materiala 1 N aqueous sodium hydroxide solution (50 ml), dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customwithout isolating
  5. custompurifying the obtained gummy substance

Sources & evidence

ORD record
ord-6e76426ace1e4384a81ea634dd877b6e
Source dataset
uspto-grants-2005_01
Patent number
US06838465B2

Reaction notes

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