Triethylamine → N-(4-Bromo-5,6,7,8-tetrahydro-8-isoquinolinyl)ethanesulfonamide

HRID 530343Notes

Reaction equation

HRID 530343 reaction equation
[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([NH2:12])[C:6]=2[CH:5]=[N:4][CH:3]=1.CCN(CC)CC.[CH2:20]([S:22](Cl)(=[O:24])=[O:23])[CH3:21]>C(Cl)Cl>[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([NH:12][S:22]([CH2:20][CH3:21])(=[O:24])=[O:23])[C:6]=2[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 717433794-Bromo-5,6,7,8-tetrahydroisoquinolin-8-amine

Product 1

HCID 89458481N-(4-Bromo-5,6,7,8-tetrahydro-8-isoquinolinyl)ethanesulfonamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (rac)-4-bromo-5,6,7,8-tetrahydro-isoquinolin-8-ylamine (intermediate A-2 [D]) (227 mg, 1 mmol) and Et3N (152 mg, 1.5 mmol) in DCM (5 mL) was added ethanesulfonyl chloride (193 mg, 1.5 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 hr before it was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water and the organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product (302 mg, 95% yield). MS: 319.0 (M+H)+.

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customthe organic layer was dried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3934dcafef544f35a44199158b8028b7
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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