Tryptamine → HCID 3725933, compound

HRID 1243276Notes

Reaction equation

HRID 1243276 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.C(N(CC)CC)C.[C:20](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:20]([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)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 1150TryptamineHCID 6456Trityl chlorideHCID 8471Triethylamine

Product 1

HCID 3725933HCID 3725933, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g of tryptamine (12.5 mmol) were dissolved in DCM (50 mL) and treated in one portion with triethylamine (1.74 mL. 12.5 mmol, 1 eq) and trityl chloride (3.44 g, 12.3 mmol). The resulting solution was stirred for 24 h at room temperature while protected from light. Volatiles were evaporated and the residue treated with aqueous HCl (1 N). The solid formed was filtered and washed with small portions of ether then dissolved in aqueous sodium hydrogen-carbonate and extracted into DCM. The organic layer was dried and evaporated to give 4.48 g (89% ) of 3-(N-trityl-(2-aminoethyl))-indole, which was used without further purification.

Workup

  1. customVolatiles were evaporated
  2. additionthe residue treated with aqueous HCl (1 N)
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with small portions of ether
  6. dissolutionthen dissolved in aqueous sodium hydrogen-carbonate
  7. extractionextracted into DCM
  8. customThe organic layer was dried
  9. customevaporated

Sources & evidence

ORD record
ord-228179ac3631451ea7f9261cd3a34edc
Source dataset
uspto-grants-2006_10
Patent number
US07119073B2

Reaction notes

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