Triethylamine → N-[2-(3-cyanophenoxy)ethyl]-1-(4-pyridyl)piperidine-4-carboxyamide

HRID 747681Notes

Reaction equation

HRID 747681 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14](O)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.NCC[O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[C:24]#[N:25].C([N:31]([CH2:34][CH3:35])[CH2:32]C)C.[OH:36]N1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[C:24]([C:23]1[CH:22]=[C:21]([CH:28]=[CH:27][CH:26]=1)[O:20][CH2:35][CH2:34][NH:31][C:32]([CH2:14][CH:11]1[CH2:10][CH2:9][N:8]([C:5]2[CH:4]=[CH:3][N:2]=[CH:7][CH:6]=2)[CH2:13][CH2:12]1)=[O:36])#[N:25]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109098773-(2-Aminoethoxy)benzonitrileHCID 162172691-(Pyridin-4-yl)piperidine-4-carboxylic acid hydrochloride

Product 1

HCID 131726962N-[2-(3-cyanophenoxy)ethyl]-1-(4-pyridyl)piperidine-4-carboxyamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

412 mg (1.48 mmol) of 1-(4-pyridyl)-piperidine-4-carboxylic acid hydrochloride, 350 mg (1.77 mmol) of 3-(2-aminoethoxy)benzonitrile, 0.25 ml (1.77 mmol) of triethylamine, 240 mg (1.77 mmol) of 1-hydroxybenzotriazole and 340 mg (1.77 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were stirred together in 3 ml of dimethylformamide at room temperature overnight. After the treatment with ethyl acetate as the extractant in an ordinary manner; the title compound was obtained.

Sources & evidence

ORD record
ord-e04a520f41fa4f9194c9c64270c28bd6
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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