2-Aminophenol → HCID 86625767, compound

HRID 1366974Notes

Reaction equation

HRID 1366974 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[OH:37]>CN(C)C=O.C(OCC)(=O)C.ON1C2C=CC=CC=2N=N1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15](=[O:17])[NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[OH:37])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 58012-AminophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 50585361-Boc-2-Piperidineacetic Acid

Product 1

HCID 86625767HCID 86625767, compoundYield 97.9%

Reagents, catalysts & solvents 3

HCID 757711-HydroxybenzotriazoleCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-carboxymethyl-piperidine-1-carboxylic acid tert butyl ester (0.97 g), (Peschke, Bernd; Ankersen, Michael; Hansen, Birgit Sehested; Hansen, Thomas Kruse; Johansen, Nils Langeland; Lau, Jesper; Madsen, Kjeld; Petersen, Hans; Thogersen, Henning; Watson, Brett. Eur. J. Med. Chem. (1999), 34(5), 363-380) in dimethylformamide (8.0 ml) was treated sequentially with EDC.HCl (0.76 g), 2-aminophenol (0.43 g) and 1-hydroxybenzotriazole (0.05 g). The mixture was stirred for 2 h, diluted with ethyl acetate and washed with water, dried (MgSO4) and solvent removed at reduced pressure to give the title compound (1.29 g) as a gum.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4) and solvent
  3. customremoved at reduced pressure

Sources & evidence

ORD record
ord-805037d3322447ac87b4aef45cea8bf0
Source dataset
uspto-grants-2011_02
Patent number
US07893090B2

Reaction notes

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