5-Methoxytryptamine → Ammonium Hydroxide

HRID 1666824Notes

Reaction equation

HRID 1666824 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]1[CH:29]=[C:28]2[C:21]([NH:22][CH:23]=[C:24]2[CH2:25][CH2:26][NH2:27])=[CH:20][CH:19]=1.[BH4-].[Na+].CCOC(C)=O>CO>[NH4+:22].[OH-:1].[CH3:16][O:17][C:18]1[CH:29]=[C:28]2[C:21](=[CH:20][CH:19]=1)[NH:22][CH:23]=[C:24]2[CH2:25][CH2:26][NH:27][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=1

Participants

7

Reactant 4

HCID 18335-MethoxytryptamineHCID 8857Ethyl AcetateHCID 382843-PhenoxybenzaldehydeHCID 4311764Sodium borohydride

Product 2

HCID 14923Ammonium HydroxideYield 2%HCID 21071637HCID 21071637, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Combine 3-phenoxybenzaldehyde (5.6 ml, 26.7 mmol), 5-methoxytryptamine (5.0 g, 26.7 mmol) and 3 Å molecular sieves (1.0 g) in methanol (50 ml) and under argon and heat at reflux for 4 hours. Remove the molecular sieves by filtration and then slowly add sodium borohydride (3.0 g, 60.0 mmol) portionwise. Stir at room temperature for 1 hour and concentrate under reduced pressure, dissolve the concentrated reaction mixture in sodium hydroxide 1N (100 ml) and extract with dichloromethane (3×50 ml). Combine organic layers and wash sequentially with distilled water (50 ml) and brine (50 ml), dry (Na2SO4) the organic layer, and concentrate to give a residue. Chromatograph the residue on silica gel eluting with 9:1 EtOAc:MeOH with 2% NH4OH gives the title compound.

Workup

  1. temperatureat reflux for 4 hours
  2. customRemove the molecular sieves
  3. filtrationby filtration
  4. concentrationconcentrate under reduced pressure
  5. dissolutiondissolve
  6. customthe concentrated reaction mixture in sodium hydroxide 1N (100 ml)
  7. extractionextract with dichloromethane (3×50 ml)
  8. washCombine organic layers and wash sequentially with distilled water (50 ml) and brine (50 ml)
  9. dry with materialdry (Na2SO4) the organic layer
  10. concentrationconcentrate
  11. customto give a residue

Sources & evidence

ORD record
ord-bacbad3a72844a068cfc59083c14d719
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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