Benzyl Alcohol → HCID 17933207, compound

HRID 842232Notes

Reaction equation

HRID 842232 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=[O:11])[CH:3]=[CH:2]1.[CH2:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:13]([O:11][C:10]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[CH:3]2)=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 742811H-Indole-7-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 17933207HCID 17933207, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.68 g (4.2 mmol) of indole-7-carboxylic acid, 0.9 g (8.4 mmol) of benzylalcohol 1.03 g (8.4 mmol) of DMAP and 1.6 g (8.4 mmol) of 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (Aldrich) in 30 mL of CH2Cl2 was stirred at rt for 18 h. The reaction mixture was concentrated and the residue was purified by chromatography (silica, hexanes:ethyl acetate 30:1) to give 0.88 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (silica, hexanes:ethyl acetate 30:1)

Sources & evidence

ORD record
ord-9f86c6ca280749eab2257d2bb56662cc
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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