Formaldehyde → Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

HRID 1508310Notes

Reaction equation

HRID 1508310 reaction equation
[CH2:1]([NH:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]=O.[C:16]([O-:19])([O-])=O.[K+].[K+]>CO>[CH2:1]([N:8]([CH2:14][O:19][CH3:16])[CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 353458N-[(Trimethylsilyl)methyl]benzylamine

Product 1

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
12.5 °C

Procedure

To a stirred solution of benzyl-trimethylsilanylmethyl-amine (Preparation 28, 25 g, 128.86 mmol) in methanol (300 mL), formaldehyde solution (37-41% w/v, 4.253 g, 141.75 mmol) was added at 0° C. Resulting reaction mixture was stirred at 0° C. for 1 hour and 10-15° C. for 3 hours. K2CO3 (21.34 g, 154.69 mmol) was added to reaction mixture and reaction was stirred at 10-15° C. for 2 hours. After complete consumption of starting material, the resulting reaction mixture was filtered through Buchner funnel; solid was washed by ethyl acetate (3×20 mL). Combined filtrate was concentrated in vacuo to afford product as faint yellow oil (23 g, Crude). Crude compound was used as such for next reaction. (m/z): 195.1 (M+H).

Workup

  1. customResulting
  2. customreaction mixture
  3. stirringwas stirred at 10-15° C. for 2 hours
  4. customAfter complete consumption of starting material
  5. customthe resulting reaction mixture
  6. filtrationwas filtered through Buchner funnel
  7. washsolid was washed by ethyl acetate (3×20 mL)
  8. concentrationCombined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7317518d491d4643b2e6a9b7aeb442c7
Source dataset
uspto-grants-2015_12
Patent number
US09221835B2

Reaction notes

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