4-Fluorobenzaldehyde → N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine

HRID 1913106Notes

Reaction equation

HRID 1913106 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][O:11][CH:12]([O:15][CH3:16])[CH2:13][NH2:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:10][O:11][CH:12]([O:15][CH3:16])[CH2:13][NH:14][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 11615438N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amineYield 93.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

12.4 g of 4-fluorobenzaldehyde were dissolved in 100 mL of toluene and reacted with 10.5 g of 2-aminoacetaldehyde dimethylacetal and 1.90 of p-toluenesulfonic acid monohydrate for two hours at a Dean Stark apparatus. The solution was allowed to cool down, extracted with saturated sodium bicarbonate, water and brine, dried over magnesium sulfate and evaporated to dryness. The crude product was dissolved in 100 mL of ethanol. 1.89 g of sodium borohydride were added portionwise. Stirring was continued overnight. For workup, acetic acid was added until no gas evolution could be observed. Then the solution was evaporated to dryness, taken up in dichloromethane and washed twice with water. The organic layer was extracted with brine, dried over magnesium sulfate and evaporated to dryness. The obtained crude product (20 g) was used for further reactions without purification. Rt=0.86 min (Method B). Detected mass: 182.1 (M-OMe−), 214.2 (M+H+).

Workup

  1. temperatureto cool down
  2. extractionextracted with saturated sodium bicarbonate, water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. dissolutionThe crude product was dissolved in 100 mL of ethanol
  6. addition1.89 g of sodium borohydride were added portionwise
  7. additionFor workup, acetic acid was added until no gas evolution
  8. customThen the solution was evaporated to dryness
  9. washwashed twice with water
  10. extractionThe organic layer was extracted with brine
  11. dry with materialdried over magnesium sulfate
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-ec2a5da65768492b98d09d54401b499e
Source dataset
uspto-grants-2013_12
Patent number
US08609691B2

Reaction notes

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