Sodium borohydride → Benzyl-(6-methoxy-naphthalen-2-ylmethyl)-amine

HRID 1357293Notes

Reaction equation

HRID 1357293 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]=[CH:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=2)[CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([NH:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=2)[CH:13]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18505309Benzyl-(6-methoxy-naphthalen-2-ylmethylene)-amine

Product 1

HCID 18505307Benzyl-(6-methoxy-naphthalen-2-ylmethyl)-amineYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.19 g, 5 mmol) was added in portions under nitrogen to a solution of benzyl-(6-methoxy-naphthalen-2-ylmethylene)-amine (1.38 g, 5 mmol), prepared in the previous step, in 150 mL of absolute ethanol at room temperature. After the addition the reaction was stirred at room temperature for 20 h (overnight). The reaction was quenched with 30 mL of 1N HCl (pH 2 by litmus paper). The solvent was removed under reduced pressure to give a solid. The solid was partitioned between methylene chloride and water. The aqueous layer was made basic with 1N NaOH. The aqueous layer was separated and extracted two times with methylene chloride. The organic extracts were combined, dried (MgSO4) and the solvent removed under reduced pressure to give benzyl-(6-methoxy-naphthalen-2-ylmethyl)-amine (1.38 g, 100%) as an off-white solid, mp 45-53° C.

Workup

  1. additionAfter the addition the reaction
  2. customThe reaction was quenched with 30 mL of 1N HCl (pH 2 by litmus paper)
  3. customThe solvent was removed under reduced pressure
  4. customto give a solid
  5. customThe solid was partitioned between methylene chloride and water
  6. customThe aqueous layer was separated
  7. extractionextracted two times with methylene chloride
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ca96113404db4603bf04cd146f8d944f
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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