Methylamine → Methyl-(1-propyl-naphthalen-2-ylmethyl)amine

HRID 1362028Notes

Reaction equation

HRID 1362028 reaction equation
[CH3:1][NH2:2].[CH2:3]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[CH:16]=O)[CH2:4][CH3:5].[BH4-].[Na+]>CO>[CH3:1][NH:2][CH2:16][C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]=1[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 12014521-Propyl-naphthalene-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amineYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.0 M methylamine in methanol (20 mL) was added to 1-propyl-naphthalene-2-carbaldehyde (0.983 g, 4.95 mmol) under N2 and allowed to stir for 18 h. The solution was concentrated under reduced pressure. Then the resulting dark yellow oil was solvated in EtOH (20 mL) under N2. To the solution was added NaBH4 (0.187 g, 4.95 mmol) and the mixture allowed to stir for 6.5 h. The reaction was concentrated under reduced pressure, then solvated in 1 N NaOH (20 mL) and extracted with Et2O (3×50 mL). The organics were combined, washed with brine (2×100 mL), dried over Na2SO4, filtered and concentrated to yield the title compound (0.94 g, 89%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.87-7.73 (m, 4H), 7.51-7.43 (m, 3H), 3.53 (m, 1H), 2.09 (s, 3H), 1.70-1.52 (m, 2H), 1.26-1.12 (m, 2H), 0.87-0.79 (m, 3H).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. stirringto stir for 6.5 h
  3. concentrationThe reaction was concentrated under reduced pressure
  4. extractionextracted with Et2O (3×50 mL)
  5. washwashed with brine (2×100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8615c197b8794451802c94fbdc56fe59
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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