Hydrochloric Acid → 1-(6-methoxynaphthalen-2-yl)-N-methylmethanamine

HRID 1357249Notes

Reaction equation

HRID 1357249 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]=[N:14][CH3:15])[CH:7]=[CH:6]2.[BH4-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:13][NH:14][CH3:15])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18505302(6-Methoxy-naphthalen-2-ylmethylene)-methyl-amine

Product 1

HCID 49623511-(6-methoxynaphthalen-2-yl)-N-methylmethanamineYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(6-Methoxy-naphthalen-2-ylmethylene)-methyl-amine (20.0 g, 100 mmol), prepared in the previous step, was dissolved with heating in 300 mL of absolute ethanol. At room temperature, sodium borohydride (3.783 g, 100 mmol) was added portion wise. The reaction stirred under nitrogen for 18 h. 1N HCl was added to the reaction until pH 1 (litmus paper). The solvent was removed under reduced pressure and the resulting residue was partitioned between methylene chloride and water. The aqueous layer was made basic with 1N NaOH. The aqueous layer was separated and extracted with methylene chloride. The combined organic extracts were dried (MgSO4) and solvent removed under reduced pressure to give (6-methoxy-naphthalen-2-ylmethyl)-methyl-amine (18.80 g, 93.5%) as an off-white solid, mp 96-104° C.

Workup

  1. dissolutionwas dissolved
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting residue was partitioned between methylene chloride and water
  4. customThe aqueous layer was separated
  5. extractionextracted with methylene chloride
  6. dry with materialThe combined organic extracts were dried (MgSO4) and solvent
  7. customremoved under reduced pressure

Sources & evidence

ORD record
ord-46f4296ba5f4491094a7ce36f1fde789
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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