Hydrochloric Acid → 249624-75-7

HRID 1264892Notes

Reaction equation

HRID 1264892 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[CH2:5][CH2:4][N:3]=1.[BH4-].[Na+].Cl>CO>[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[CH2:5][CH2:4][NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18613806HCID 18613806, compound

Product 1

HCID 12991370249624-75-7Yield 82.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 1-methyl-7-fluoro-3,4-dihydroisoquinoline (2.4 g, 14.7 mmol) prepared in Step 2 in methanol (10 ml), sodium borohydride (0.28 g, 1 eq.) was portionwise added. The reaction mixture was stirred for 3 hours and 1N hydrochloric acid solution (20 ml) was added thereto. The reaction mixture was washed with dichloromethane. The water layer was adjusted to pH 12 with potassium hydroxide solution and extracted with dichloromethane. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give 2.0 g of the titled compound.

Workup

  1. washThe reaction mixture was washed with dichloromethane
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f8ebdc84a904294a02227f074a998f7
Source dataset
uspto-grants-2003_04
Patent number
US06545008B1

Reaction notes

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