Acetic Acid → 1-naphthalenemethanamine, n,n-dimethyl-

HRID 2360719Notes

Reaction equation

HRID 2360719 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CC([O-])=O.[Na+].[NH:18]([CH3:20])[CH3:19].Cl.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1>[CH3:19][N:18]([CH3:20])[CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 61951-NaphthaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 2649531-naphthalenemethanamine, n,n-dimethyl-Yield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-naphthaldehyde (1.50 g, 9.62 mmol, 1.00 equiv) in 40 mL THF is added NaOAc (0.79 g, 9.62 mmol, 1.00 equiv), Me2NH.HCl (863 mg, 10.6 mmol, 1.10 equiv), and AcOH (0.11 mL, 1.9 mmol, 0.20 equiv) at 23° C. NaBH(OAc)3 (4.08 g, 19.3 mmol, 2.00 equiv) is added in three portions over five minutes. The suspension is stirred for 12 hours before solvent is removed in vacuo. To the residue is added 10 mL sat. NaHCO3(aq) and 10 mL CH2Cl2. The phases are separated and the aqueous phase is extracted with CH2Cl2 (3×10 mL). The combined organic phase is concentrated in vacuo. The residue is purified by chromatography on silica gel eluting with hexanes/EtOAc 3:2 (v/v) to afford 1.64 g of the title compound as a colorless liquid (92% yield).

Workup

  1. customis removed in vacuo
  2. additionTo the residue is added 10 mL sat. NaHCO3(aq) and 10 mL CH2Cl2
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with CH2Cl2 (3×10 mL)
  5. concentrationThe combined organic phase is concentrated in vacuo
  6. customThe residue is purified by chromatography on silica gel eluting with hexanes/EtOAc 3:2 (v/v)

Sources & evidence

ORD record
ord-2fcfad24e6e447e4a4f3da52905adbaf
Source dataset
uspto-grants-2014_04
Patent number
US08686158B2

Reaction notes

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