Acetyl chloride → HCID 86685954, compound

HRID 2277660Notes

Reaction equation

HRID 2277660 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.[C:20](Cl)(=[O:22])[CH3:21]>C(Cl)Cl>[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([NH:12][C:20](=[O:22])[CH3:21])[C:6]=2[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 717433794-Bromo-5,6,7,8-tetrahydroisoquinolin-8-amine

Product 1

HCID 86685954HCID 86685954, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-amine (intermediate B-12 [A], 318 mg, 1.4 mmol) and Et3N (3.0 mL) in DCM (10 mL) was added acetyl chloride (0.106 mL, 1.4 mmol) at 0° C. and stirring was continued at 0° C. for 1 hour. The resulting mixture was extracted with EtOAc (2×100 mL). The combined organics were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to afford a crude product which was purified by silica gel flash chromatography eluting with a 0 to 50% EtOAc-heptane gradient to give the title compound (346 mg, 92%) as light yellow solid. MS: 269.1 & 271.1 (M+H+).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×100 mL)
  2. washThe combined organics were washed with brine
  3. customdried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo
  6. customto afford a crude product which
  7. customwas purified by silica gel flash chromatography
  8. washeluting with a 0 to 50% EtOAc-heptane gradient

Sources & evidence

ORD record
ord-a67f6b8314fd4ad18fb076547ca293b6
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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