Triethylamine → 4-(4-Chloro-phenoxymethyl)-benzylamine

HRID 2097353Notes

Reaction equation

HRID 2097353 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:11]([CH2:12][N:13]=[N+]=[N-])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CCN(CC)CC.Cl[Sn]Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24479Stannous ChlorideHCID 231324374-(4-Chlorophenoxymethyl)-benzylazide

Product 1

HCID 231324444-(4-Chloro-phenoxymethyl)-benzylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4-Chloro-phenoxymethyl)-benzylazide (3.2 g, 11.7 mmol) was dissolved in MeOH (50 mL). NEt3 (11.35 mL, 81.9 mmol) and SnCl2×2H2O (5.28 g, 23.4 mmol) were added and the exothermic reaction was stirred under reflux. When boiling ceased the mixture was heated to reflux for additional 45 min. After cooling to r.t. the mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in CH2Cl2 (300 mL) and this solution was washed with sat. aq. NaHCO3-solution (1×100 mL), dried over Na2SO4, filtered and evaporated to dryness to give the title compound, pure enough for further reaction.

Workup

  1. customthe exothermic reaction
  2. temperatureunder reflux
  3. temperaturewas heated
  4. temperatureto reflux for additional 45 min
  5. filtrationwas filtered
  6. customthe filtrate was evaporated to dryness
  7. dissolutionThe residue was dissolved in CH2Cl2 (300 mL)
  8. washthis solution was washed with sat. aq. NaHCO3-solution (1×100 mL)
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-5dc0a59858f2425ea9ecd12ec1d888fd
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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