Tryptamine → HCID 17447799, compound

HRID 1095548Notes

Reaction equation

HRID 1095548 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.[CH:13]1([N:18]=[C:19]=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]1>CC(C)=O.C(N(CC)CC)C>[CH:13]1([NH:18][C:19]([NH:1][CH2:2][CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 1150TryptamineHCID 643500Cyclopentyl Isocyanate

Product 1

HCID 17447799HCID 17447799, compoundYield 34.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8471TriethylamineSolvent

Procedure

Tryptamine (1.04 g, 6.5 mmol) was dissolved in a mixture of acetone (20 ml) and triethylamine (1 ml) under a nitrogen atmosphere. Cyclopentyl isocyanate (795 mg, 7.15 mmol, 0.81 ml) was swiftly added dropwise at 0° C. and the mixture was then subsequently stirred for 2H, while cooling with ice, and at RT overnight. A white solid had precipitated out of the solution, and was filtered off with suction and rinsed with acetone. It was 641 mg of pure product. The filtrate was concentrated i. vac. and the residue was then stirred thoroughly with acetone (10 ml). The undissolved white solid was filtered off with suction and rinsed with acetone, and a further 612 mg of pure product were obtained in this way.

Workup

  1. temperaturewhile cooling with ice
  2. customat RT
  3. customovernight
  4. customA white solid had precipitated out of the solution
  5. filtrationwas filtered off with suction
  6. washrinsed with acetone
  7. concentrationThe filtrate was concentrated i
  8. stirringand the residue was then stirred thoroughly with acetone (10 ml)
  9. filtrationThe undissolved white solid was filtered off with suction
  10. washrinsed with acetone

Sources & evidence

ORD record
ord-45bad8735df8446db176dbb0aaa94f88
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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