Tryptamine → Tryptamide

HRID 1095550

Reaction equation

HRID 1095550 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.Cl.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1>C1COCC1>[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][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=2)=[CH:5]1

Participants

4

Reactant 2

HCID 1150TryptamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

Product 1

HCID 65768Tryptamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tryptamine (640 mg, 4.0 mmol) was initially introduced into abs. THF (30 ml). TEA (596 μl, 4.3 mmol) and nicotinic acid chloride hydrochloride (770 mg, 4.3 mmol) was then added and the mixture was stirred at RT for 5 h. The mixture was concentrated to dryness i. vac. The residue was taken up in EA (20 ml) and the mixture was washed with saturated NaHCO3 solution (2×20 ml) and with NaCl solution (2×20 ml). The organic phase was dried over Na2SO4 and concentrated i. vac. Yield: 482 mg (45%)

Workup

  1. concentrationThe mixture was concentrated to dryness i
  2. washthe mixture was washed with saturated NaHCO3 solution (2×20 ml) and with NaCl solution (2×20 ml)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated i

Sources & evidence

ORD record
ord-84a9b1ea3e754e9fb269f3e7044c6d71
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Linked notes

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