1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10109961, compound

HRID 842027Notes

Reaction equation

HRID 842027 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.[C:13]([C:18]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)(=[O:17])[CH2:14][CH2:15][CH3:16].CCN=C=NCCCN(C)C>ClCCl.CN(C1C=CN=CC=1)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([N:21]3[CH2:22][CH2:23][C:18]([C:13](=[O:17])[CH2:14][CH2:15][CH3:16])([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:19][CH2:20]3)=[O:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 742801H-Indole-5-Carboxylic AcidHCID 414350HCID 414350, compound

Product 1

HCID 10109961HCID 10109961, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Indole-5-carboxylic acid (177 mg, 1.1 mmole) and 4-butyryl-4-phenylpiperidine (231 mg, 1.0 mmole) were dissolved in 10 ml dichloromethane. To this solution was added catalytic DMAP and EDCI (330 mg, 1.1 mmole). The resulting solution was then stirred at room temperature overnight. The reaction was worked up by washing sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride. The compound was then purified by flash chromatography on silica gel (40:1 CHCl3/MeOH). 1H NMR (300 Mhz, CDCl3) δ 8.60 (s, 1H), 7.66 (d, 1H), 7.38-7.18 (m, 8H), 6.53 (d, 1H), 4.28 (bs, 1H), 3.67 (bs, 1H), 3.39 (t, 2H), 2.42 (bs, 2H), 2.18 (m, 3H), 1.88 (bs, 1H), 1.41 (m, 2H), 0.66 (t, 3H).

Workup

  1. washby washing sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride
  2. customThe compound was then purified by flash chromatography on silica gel (40:1 CHCl3/MeOH)

Sources & evidence

ORD record
ord-1060505e8daf4aa68bc75d819a9b7dd8
Source dataset
uspto-grants-2002_04
Patent number
US06372752B1

Reaction notes

Loading…