Triethylamine → HCID 67059646, compound

HRID 1807729Notes

Reaction equation

HRID 1807729 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[Cl:11].[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>ClCCl.C(OCC)(=O)C.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)=[O:8])=[CH:4][C:3]=1[Cl:11]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 172114-Amino-3-chlorobenzoic acidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67059646HCID 67059646, compoundYield 77.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 4-amino-3-chlorobenzoic acid (58.3 mmol, 10 g), tert-butyl piperazine-1-carboxylate (58.3 mmol, 10.86 g) and triethylamine (146 mmol, 20.31 mL, 14.74 g) in dichloromethane (200 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (69.9 mmol, 13.41 g). The reaction was stirred for 24 hours then was diluted with ethyl acetate and water. The organic layer was separated, dried (magnesium sulfate) and concentrated under reduced pressure. Diethyl ether was added and the solid was filtered off to give the title compound (15.4 g).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. additionDiethyl ether was added
  5. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-0f07a1c352064d1d97035ca562915eea
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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