1-(3-Aminopropyl)-4-methylpiperazine → HCID 58779629, compound

HRID 1372380Notes

Reaction equation

HRID 1372380 reaction equation
[CH:1]([C:3]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([OH:11])=O)[C:4]=1[CH3:12])=[O:2].[NH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1>>[CH3:23][N:20]1[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][CH2:14][NH:13][C:9]([C:5]2[C:4]([CH3:12])=[C:3]([CH:1]=[O:2])[NH:7][C:6]=2[CH3:8])=[O:11])[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 110737925-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid

Product 1

HCID 58779629HCID 58779629, compoundYield 23%

Procedure

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (1.0 g, 6 mmol) was reacted with 1-(3-aminopropyl)-4-methylpiperazine (1.06 mL) to give 0.38 g (23% yield) of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid [3-(4-methyl-piperazin-1-yl)-propyl]-amide using General Amidation Procedure 1. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 11.8 (br s, 1H, NH), 9.52 (s, 1H, CHO), 7.52 (m, 1H, CONH), 3.2 (m, 2H, CH2), 2.8 (m, 2H, CH2), 2.5 (m, 8H, 4×CH2), 2.34 (s, 3H, CH3), 2.29 (s, 3H, CH3), 1.68 (m, 2H, CH2). MS m/z 307 [M+1].

Sources & evidence

ORD record
ord-5ebab59cd6994fd480ef54f588e889c7
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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