Tryptamine → HCID 3775371, compound

HRID 2355143Notes

Reaction equation

HRID 2355143 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]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)[CH2:14][CH2:15][CH3:16].[CH2:27](N(CC)CC)C>C(Cl)Cl>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][NH:1][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])=[CH:5]1

Participants

5

Reactant 3

HCID 1150TryptamineHCID 8471TriethylamineHCID 27373524-Butylbenzene-1-sulfonyl chloride

Product 1

HCID 3775371HCID 3775371, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tryptamine (19.2 mg, 0.12 mmol) in 2 ml CH2Cl2 was added 0.06 mmol of 4-n-butylphenylsulfonyl chloride in CH2Cl2, followed by 16.5 μl of triethylamine. After stirring the reaction for 6 hr at room temperature, the mixture was purified by loading on to a cation exchange resin and the resin was eluted using CH2Cl2. The appropriate fractions were combined and evaporated to give the product. 1H NMR (CDCl3): δ 0.89 (t, 3H), 1.3 (m, 4H), 1.6 (m, 2H), 2.65 (t, 2H), 2.96 (t, 2H), 3.3 (m, 2H), 6.9-7.4 (m, 6H), 7.6 (d, 2H), 8.0 (s, 1H).

Workup

  1. customthe reaction for 6 hr at room temperature
  2. customthe mixture was purified by loading on to a cation exchange resin
  3. washthe resin was eluted
  4. customevaporated
  5. customto give the product

Sources & evidence

ORD record
ord-9b924c111ec545d8afc4e8a5169ec7fb
Source dataset
uspto-grants-2010_07
Patent number
US07754755B2

Reaction notes

Loading…