Methylamine → HCID 12027889, compound

HRID 575907Notes

Reaction equation

HRID 575907 reaction equation
[CH3:1][NH2:2].[CH2:3]([O:5][CH:6]([O:15][CH2:16][CH3:17])[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)[CH3:4].[BH4-].[Na+].[OH-].[Na+]>CO>[CH2:3]([O:5][CH:6]([O:15][CH2:16][CH3:17])[C:7]1[CH:14]=[CH:13][C:10]([CH2:11][NH:2][CH3:1])=[CH:9][CH:8]=1)[CH3:4]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 5959934-(Diethoxymethyl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12027889HCID 12027889, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

2M methylamine in MeOH (288.1 mL, 576.2 mmol) was diluted with methanol (1.000 L) and stirred at ˜20° C. 4-(Diethoxymethyl)benzaldehyde (100 g, 480.2 mmol) was added dropwise over 1 minute and the reaction stirred at ambient temperature for 1.25 hours. Sodium borohydride (29.07 g, 30.76 mL, 768.3 mmol) was added portionwise over 20 minutes while maintaining the temperature between 20 and 30° C. with an ice-water bath. The reaction solution was stirred at ambient temperature overnight then quenched by the dropwise addition of NaOH (960.4 mL of 1.0 M, 960.4 mmol) over 20 minutes. The reaction was stirred for 30 minutes and concentrated in vacuo to remove MeOH. The reaction was partitioned with MTBE (1.200 L) and the phases separated. The organic phase was washed with water (300.0 mL), dried (Na2SO4), and concentrated in vacuo to give the title compound as a yellow oil (102.9 g, 96% Yield); 1H NMR (400 MHz, CDCl3) δ 1.25 (t, 6H), 2.46 (s, 3H), 3.45-3.65 (m, 4H), 3.75 (s, 2H), 5.51 (s, 1H), 7.32 (d, 2H) and 7.44 (d, 2H) ppm.

Workup

  1. stirringthe reaction stirred at ambient temperature for 1.25 hours
  2. temperaturewhile maintaining the temperature between 20 and 30° C. with an ice-water bath
  3. stirringThe reaction solution was stirred at ambient temperature overnight
  4. stirringThe reaction was stirred for 30 minutes
  5. concentrationconcentrated in vacuo
  6. customto remove MeOH
  7. customThe reaction was partitioned with MTBE (1.200 L)
  8. customthe phases separated
  9. washThe organic phase was washed with water (300.0 mL)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33a6d35f2e9b4c63892c94f087a70898
Source dataset
uspto-grants-2015_05
Patent number
US09035053B2

Reaction notes

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