1-Hydroxybenzotriazole → N-(12-hydroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

HRID 1003306Notes

Reaction equation

HRID 1003306 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]([O-:17])=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[K+].[NH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[OH:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][NH:19][C:15]([C:12]1[CH:13]=[N:14][C:9]([N:6]2[CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:8][CH2:7]2)=[CH:10][CH:11]=1)=[O:17]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 518202012-Amino-1-dodecanolHCID 23663822Potassium 6-(4-ethyl-1-piperazinyl)pyridine-3-carboxylate

Product 1

HCID 15462624N-(12-hydroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4.07 g of potassium 6-(4-ethyl-1-piperazinyl)-pyridine-3-carboxylate and 3.00 g of 12-aminododecanol was added 50 ml of methylene chloride and then 2.86 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSCI) and 2.01 g of 1-hydroxybenzotriazole (HOBt) were added while stirring at room temperature. The mixture was stirred at room temperature for 15 hours. To the reaction solution were added water and diisopropyl ether and subsequent filtration and drying under reduced pressure afforded 5.67 g of the title compound as a crystal.

Workup

  1. stirringThe mixture was stirred at room temperature for 15 hours
  2. additionTo the reaction solution were added
  3. filtrationwater and diisopropyl ether and subsequent filtration
  4. customdrying under reduced pressure

Sources & evidence

ORD record
ord-88bf458d576b487990051a158e02cd63
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

Loading…