Pyrrole-2-Carboxylic Acid → 1-(Pyrrole-2-carbonyl)-4-[N-ethyl-N-(3-ethylamino-2-pyridinyl) amino]methylpiperidine

HRID 361850Notes

Reaction equation

HRID 361850 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.[CH2:9]([N:11]([CH2:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:12]1[C:17]([NH:18][CH2:19][CH3:20])=[CH:16][CH:15]=[CH:14][N:13]=1)[CH3:10]>>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:25]1[CH2:24][CH2:23][CH:22]([CH2:21][N:11]([CH2:9][CH3:10])[C:12]2[C:17]([NH:18][CH2:19][CH3:20])=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:27][CH2:26]1)=[O:8]

Participants

3

Reactant 2

HCID 12473Pyrrole-2-Carboxylic AcidHCID 542336454-[N-ethyl-N-(3-ethylamino-2-pyridinyl)aminomethyl]piperidine

Product 1

HCID 538802821-(Pyrrole-2-carbonyl)-4-[N-ethyl-N-(3-ethylamino-2-pyridinyl) amino]methylpiperidine

Procedure

Following the general procedure of EXAMPLE 149 and making non-critical variations, but using pyrrole-2-carboxylic acid (823 mg, 7.40 mmol) and 4-[N-ethyl-N-(3-ethylamino-2-pyridinyl)aminomethyl]piperidine (970 mg, 3.70 mmol), a crude product is obtained. Chromatography [with 40-100% ethyl acetate/hexane], followed by crystallization from ether/hexane gives the title compound, mp=109°-110°.

Workup

  1. customa crude product is obtained
  2. customChromatography [with 40-100% ethyl acetate/hexane], followed by crystallization from ether/hexane

Sources & evidence

ORD record
ord-cf4487aa3ab64ba8a66789ce75327117
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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