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

HRID 2261708Notes

Reaction equation

HRID 2261708 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH3:7]O.C=O.[CH2:11]([NH:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCCCC>[CH2:11]([N:18]([CH2:7][O:4][CH3:1])[CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 11430Potassium CarbonateHCID 353458N-[(Trimethylsilyl)methyl]benzylamine

Product 1

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
0 °C

Procedure

2.50 g (0.018 mol) of potassium carbonate, 30.4 g (0.95 mol) of methanol and 15.0 g (0.50 mol) of paraformaldehyde are initially charged and cooled to 0° C. At this temperature, within 30 min, 96.7 g (0.50 mol) of benzyltrimethylsilanylmethylamine are metered in. The biphasic reaction mixture is stirred at 0° C. for a further 1 h and then warmed to room temperature within 20 min. Within 1 min, 190.9 g of pentane are metered in. The biphasic reaction mixture is separated and the upper, organic phase is dried azeotropically for 2 h. The organic phase is concentrated and then fractionally distilled. Yield 105.9 g (89%) of a colorless liquid. −b.p. 94° C./1 mbar. −1H NMR (C6D6): δ=0.09 (s, 9 H), 2.21 (s, 2 H), 3.00 (s, 3 H), 3.75 (s, 2 H), 3.87 (s, 2 H), 7.10-7.45 (m, 5 H).

Workup

  1. customThe biphasic reaction mixture
  2. temperaturewarmed to room temperature within 20 min
  3. waitWithin 1 min
  4. customThe biphasic reaction mixture
  5. customis separated
  6. customthe upper, organic phase is dried azeotropically for 2 h
  7. concentrationThe organic phase is concentrated
  8. distillationfractionally distilled

Sources & evidence

ORD record
ord-29b8fd2b516648fa967dd040f15a4628
Source dataset
uspto-grants-2010_12
Patent number
US07847117B2

Reaction notes

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