Benzylamine → N-(Phenylmethyl)-1H-indole-5-carboxamide

HRID 973963Notes

Reaction equation

HRID 973963 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1.O.[Cl-].[Na+]>[C:14]1([CH2:13][NH:20][C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][CH:2]=[CH:3]3)=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 7504BenzylamineHCID 742801H-Indole-5-Carboxylic Acid

Product 1

HCID 19987306N-(Phenylmethyl)-1H-indole-5-carboxamideYield 85.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Indole-5-carboxylic acid (3.0 g) in anhydrous terahydrofuran (THF) (25 ml) was treated with 1,1-carbonyldiimidazole (CDI) (3.35 g) with stirring at room temperature for 1 h. A further amount (1.0 g) of CDI was added and, after stirring for a further 1H, benzylamine (4.0 g) was introduced. Stirring was continued for 24 h. The solution was diluted with water (50 ml), saturated with sodium chloride, and the THF layer separated off. The organic solution was washed with 1N hydrochloride acid (3×50 ml), brine (2×50 ml), dried (MgSO4) and evaporated under reduced pressure to given an oil (6.0 g) which was chromatographed on silica (Merck 7734, 200 g) eluting with methylene chloride and then methylene chloride/methanol (50:1) to give a foam (4.0 g). Crystallization from ethyl acetate/petroleum/ether (b.p. 60°-80°) gave the title compound as a solid (2.05 g) m.p. 155°-160°.

Workup

  1. additionwas introduced
  2. stirringStirring
  3. waitwas continued for 24 h
  4. customthe THF layer separated off
  5. washThe organic solution was washed with 1N hydrochloride acid (3×50 ml), brine (2×50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customwas chromatographed on silica (Merck 7734, 200 g)
  9. washeluting with methylene chloride

Sources & evidence

ORD record
ord-c6eaa4b9f4874a3494bc186f1c935077
Source dataset
uspto-grants-1991_11
Patent number
US05066660

Reaction notes

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