4-Bromobenzaldehyde → N-(4-Bromobenzyl)-2,2-dimethoxyethanamine

HRID 1621280

Reaction equation

HRID 1621280 reaction equation
[Br: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.[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:14][CH2:13][CH:12]([O:15][CH3:16])[O:11][CH3:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 707414-BromobenzaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 521998p-Toluenesulfonic acid monohydrateHCID 4311764Sodium borohydride

Product 1

HCID 59226241N-(4-Bromobenzyl)-2,2-dimethoxyethanamineYield 81.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

50 g (270.2 mmol) 4-bromobenzaldehyde were dissolved in 200 ml toluene and 28.4 g (270.2 mmol) aminoacetaldehyde dimethylacetal were added. After the addition of 5.1 g (27.0 mmol) p-toluenesulfonic acid monohydrate, the reaction mixture was heated under reflux in a Dean Stark apparatus. After 4 h, the reaction was cooled to room temperature and washed with saturated NaHCO3-solution (2×) and H2O. The combined aqueous layers were extracted with toluene and the combined organic layers were dried with MgSO4 and evaporated. The residue was dissolved in 200 ml ethanol and 5.11 g (135.1 mmol) sodium borohydride were added in small portions. After stirring for 2 h at room temperature and standing overnight, 5.0 ml acetic acid were added and the solvent was removed i. vac. The residue was taken up in dichloromethane and washed (2×) with H2O. After drying with MgSO4 and evaporation, 60.5 g of the title compound were obtained, which were used without further purification. Rt=0.80 min (Method C). Detected mass: 274.1/276.1 (M+H+).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux in a Dean Stark apparatus
  3. washwashed with saturated NaHCO3-solution (2×) and H2O
  4. extractionThe combined aqueous layers were extracted with toluene
  5. dry with materialthe combined organic layers were dried with MgSO4
  6. customevaporated
  7. dissolutionThe residue was dissolved in 200 ml ethanol
  8. waitstanding overnight
  9. customthe solvent was removed i
  10. washwashed (2×) with H2O
  11. dry with materialAfter drying with MgSO4 and evaporation

Sources & evidence

ORD record
ord-26c8e196576c44448c8d7df0f7a80c7f
Source dataset
uspto-grants-2014_07
Patent number
US08772492B2

Linked notes

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