Formaldehyde → HCID 57864755, compound

HRID 2425530Notes

Reaction equation

HRID 2425530 reaction equation
[CH3:1][Si:2]([CH2:5][NH:6][CH2:7][CH2:8][CH2:9][CH3:10])([CH3:4])[CH3:3].[CH2:11]=O.CO.[C:15]([O-:18])([O-])=O.[K+].[K+]>CC(OC)(C)C>[CH3:11][O:18][CH2:15][N:6]([CH2:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 11430Potassium CarbonateHCID 417546HCID 417546, compound

Product 1

HCID 57864755HCID 57864755, compoundYield 152.9%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

N-(trimethylsilyl)methyl-1-butanamine (12.5 g; max. 66.0 mmol) was added dropwise to a mixture of 37% aqueous formaldehyde (5.4 g) and methanol (2.2 g) while stirring at 0° C. After the addition was complete the reaction mixture was stirred for 90 minutes at 0° C. K2CO3 (6 g) was added and the mixture was stirred for an additional 2 hours. Then, tBME (100 ml) was added and the organic layer was separated. The aqueous layer was washed with tBME (50 ml). The combined organic layers were dried with Na2SO4. Evaporation at 75° C. under vacuum at 450 mbar gave the crude product N-(methoxymethyl)-N-((trimethylsilyl)methyl)butan-1-amine (13.5 g) as an oil in quantitative yield. The product was used without further purification.

Workup

  1. additionAfter the addition
  2. stirringwas stirred for 90 minutes at 0° C
  3. stirringthe mixture was stirred for an additional 2 hours
  4. customthe organic layer was separated
  5. washThe aqueous layer was washed with tBME (50 ml)
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. customEvaporation at 75° C. under vacuum at 450 mbar

Sources & evidence

ORD record
ord-2b0737ed752d4c469785374c44c37b94
Source dataset
uspto-grants-2011_06
Patent number
US07964739B2

Reaction notes

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