HCID 59323234, compound → N-benzyl-2-[3-benzyl-6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine

HRID 2390041Notes

Reaction equation

HRID 2390041 reaction equation
[CH2:1]([N:8]([CH2:16][CH2:17][N:18]1[CH:27]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([F:35])[CH:24]=2)[CH2:19]1)C(=O)OC(C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl.C(OCC)(=O)C>[CH2:1]([NH:8][CH2:16][CH2:17][N:18]1[CH:27]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([F:35])[CH:24]=2)[CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 59323234HCID 59323234, compound

Product 1

HCID 59323301N-benzyl-2-[3-benzyl-6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl]ethanamineYield 99%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

13 mg of tert-butyl benzyl[2-[3-benzyl-6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl]ethyl]carbamate was dissolved in 0.5 mL of a 4N hydrochloric acid-ethyl acetate solution, followed by continuously stirring at room temperature for 30 minutes. The reaction liquid was concentrated under reduced pressure, dissolved in ethyl acetate, washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (chloroform:methanol=10:1) to obtain 10 mg (yield 99%) of a title compound as a light yellow oily substance.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with an aqueous sodium bicarbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified

Sources & evidence

ORD record
ord-7b9eda15d94148a992a5af80b115e591
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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