N-bromobutanimide → 7-Amino-8-bromo-2,4,4-trimethyl-1,2,3,4-tetrahydroisoquinoline

HRID 2297607Notes

Reaction equation

HRID 2297607 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][N:8]([CH3:12])[CH2:9]2)=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(#N)C.O>[NH2:1][C:2]1[C:11]([Br:15])=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][N:8]([CH3:12])[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 18382547HCID 18382547, compound

Product 1

HCID 183825617-Amino-8-bromo-2,4,4-trimethyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 7-amino-2,4,4-trimethyl-1,2,3,4-tetrahydroisoquinoline from D3 (7 g) in acetonitrile (200 ml), was added N-bromo succinimide (7.21 g) portionwise over 10 min. The reaction mixture was cooled in an ice/methanol bath to prevent any large exotherm. and then stirred under argon for 45 min. The reaction was allowed to warm to 25° C., diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and evaporated to dryness in vacuo. The resultant brown solid was purified using dry flash column chromatography with ethyl acetate. Combination of appropriate fractions gave the title compound as an orange gum (3.95 g).

Workup

  1. temperatureThe reaction mixture was cooled in an ice/methanol bath
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness in vacuo
  6. customThe resultant brown solid was purified
  7. dry with materialusing dry flash column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-f2961e842fcf43a081945c59f309fab6
Source dataset
uspto-grants-2002_12
Patent number
US06492378B1

Reaction notes

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