Tryptamine → HCID 640227, compound

HRID 1034255Notes

Reaction equation

HRID 1034255 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.O>[CH2:13]([O:20][C:21]([NH:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 1150TryptamineHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 640227HCID 640227, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of tryptamine 1.0 g (6.2 mmol) in a mixture of CHCl3 and H2O, was added 1.1 g (6.2 mmol) benzylchloroformate, followed by dropwise addition of sat. NaHCO3 solution to maintain alkaline conditions. The reaction was stirred for 2 hrs. The reaction was extracted with CHCl3 and the organic layer was concentrated to dryness giving a dark yellow oil. The oil was crystallized from ethanol/water to give an off-white crystalline product.

Workup

  1. temperatureto maintain alkaline conditions
  2. extractionThe reaction was extracted with CHCl3
  3. concentrationthe organic layer was concentrated to dryness
  4. customgiving a dark yellow oil
  5. customThe oil was crystallized from ethanol/water
  6. customto give an off-white crystalline product

Sources & evidence

ORD record
ord-cc56f2da72c246479e659a3187128700
Source dataset
uspto-grants-1994_05
Patent number
US05314908

Reaction notes

Loading…