Triethylamine → HCID 13854273, compound

HRID 1607569Notes

Reaction equation

HRID 1607569 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=O)=[CH:3][CH:2]=1.C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.[NH2:29][CH:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][C:38]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[NH:40][CH:39]=2)[CH2:32][CH2:31]1>C1COCC1>[NH:40]1[C:41]2[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:38]([CH2:37][CH2:36][N:33]2[CH2:32][CH2:31][CH:30]([NH:29][C:11]([C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=[CH:2][CH:3]=3)=[O:13])[CH2:35][CH2:34]2)=[CH:39]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 102434-Quinolinecarboxylic acidHCID 62365Isobutyl chloroformateHCID 2154154-Piperidinamine, 1-(2-(1H-indol-3-yl)ethyl)-, hydrate

Product 1

HCID 13854273HCID 13854273, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of quinoline-4-carboxylic acid (0.87g, 5.03 mmol) and triethylamine (0.6g, 5.94 mmol) in dry THF (10 cm3) was stirred at -20° C. while a solution of isobutylchloroformate (0.65g, 5.01 mmol) was added dropwise. The mixture was allowed to warm to room temperature over 31/2 hours then was cooled to -20° C. again and a solution of 3-[2-(4-amino-1-piperidyl)ethyl]indole (1.2g, 4.94 mmol) in dry THF (20 cm3) was added dropwise. The mixture was stirred at room temperature overnight then the solvent was evaporated and the residue triturated with water and aqueous potassium carbonate to give 1.39g of crude title compound.

Workup

  1. additionwas added dropwise
  2. temperaturethen was cooled to -20° C. again
  3. customthe solvent was evaporated
  4. customthe residue triturated with water and aqueous potassium carbonate

Sources & evidence

ORD record
ord-15430b0c00854ac8bc61ceb61ad39822
Source dataset
uspto-grants-1989_09
Patent number
US04866075

Reaction notes

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