3-Ethoxybenzaldehyde → N-(2-(3-Chlorophenyl)ethyl)-3-ethoxybenzylamine

HRID 1371884Notes

Reaction equation

HRID 1371884 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)[CH3:2].[Cl:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][NH2:21])[CH:16]=[CH:17][CH:18]=1.[BH4-].[Na+]>C(O)C>[Cl:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][NH:21][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 899083-EthoxybenzaldehydeHCID 1393813-ChlorophenethylamineHCID 4311764Sodium borohydride

Product 1

HCID 21071619N-(2-(3-Chlorophenyl)ethyl)-3-ethoxybenzylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 3-ethoxybenzaldehyde (3.38 g, 22.5 mmol), 2-(3-chlorophenyl)ethylamine (2.33 g, 15.0 mol), and 3 Å molecular sieves (2.88 g) in ethanol (230 ml). Stir the reaction mixture at reflux for 4 hours. Filter to remove the molecular sieves and then slowly add sodium borohydride (1.70 g, 45.0 mmol) to the filtrate and stir at ambient temperature. After 15 hours, concentrate the reaction mixture to a residue, dissolve the residue in 1N NaOH, and extract with dichloromethane. Combine organic extracts, wash with brine, dry over Na2SO4, and concentrate to a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound. The HCl salt was prepared in ethyl acetate to give the title compound: mp 178–180° C.; MS (ACPI): m/e 290.1 (M+1); Analysis for C17H21Cl2NO: Calcd: C, 62.58; H, 6.49; N, 4.29; Found: C, 62.65; H, 6.53; N, 4.32.

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationFilter
  3. customto remove the molecular sieves
  4. concentrationconcentrate the reaction mixture to a residue
  5. dissolutiondissolve the residue in 1N NaOH
  6. extractionextract with dichloromethane
  7. washCombine organic extracts, wash with brine
  8. dry with materialdry over Na2SO4
  9. concentrationconcentrate to a residue

Sources & evidence

ORD record
ord-217cd848d5f8419fbb61266eff4a4559
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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