Tryptamine → HCID 58615650, compound

HRID 2355144Notes

Reaction equation

HRID 2355144 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.Cl[S:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>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:21]([C:24]2[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:31][CH:32]=2)(=[O:23])=[O:22])=[CH:5]1

Participants

5

Reactant 3

HCID 1150TryptamineHCID 8471TriethylamineHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 58615650HCID 58615650, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3.0 g (18.7 mmol) of tryptamine in 20 ml of CH2Cl2 was added, 2.5 ml (18.7 mmol) of triethylamine followed by 2.06 g (9.4 mmol) of 4-(chlorosulphonyl) benzoic acid. After stirring for 2 h, the mixture was extracted with CH2Cl2 (3×50 ml) and the combined organic extracts were washed with water and dried and evaporated. The residue was chromatographed on silica gel using 2:98:0.5 MeOH/CH2Cl2/AcOH to afford the title compound as a solid. MS m/e 345; HPLC retention time 2.52 min.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×50 ml)
  2. washthe combined organic extracts were washed with water
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed on silica gel using 2:98:0.5 MeOH/CH2Cl2/AcOH

Sources & evidence

ORD record
ord-36e261d5935d4c8ea4f13f408edcc32d
Source dataset
uspto-grants-2010_07
Patent number
US07754755B2

Reaction notes

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