3-Phenylpropylamine → 5-Hydroxypyridine-2-carboxylic acid (3-phenylpropyl)amide

HRID 389973

Reaction equation

HRID 389973 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.[C:43]1([CH2:49][CH2:50][CH2:51][NH2:52])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>ClCCl>[C:43]1([CH2:49][CH2:50][CH2:51][NH:52][C:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][N:6]=2)=[O:10])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

7

Reactant 5

HCID 162593-PhenylpropylamineHCID 81531DiisopropylethylamineHCID 2687405-Hydroxypyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 860284705-Hydroxypyridine-2-carboxylic acid (3-phenylpropyl)amideYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-hydroxypyridine-2-carboxylic acid (0.103 g, 0.74 mmol) in dichloromethane was added diisopropylethylamine (0.279 mL, 1.6 mmol), followed by 1-hydroxybenzotriazole monohydrate (0.012 g, 0.8 mmol) and EDCl (0.153 g, 0.8 mmol). The resulting mixture was stirred for 15 minutes and 3-phenyl-1-propylamine (0.108 g, 0.8 mmol) was added. After stirring for 22 h, the reaction mixture was diluted with dichloromethane (80 mL), washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by column chromatography afforded 5-hydroxypyridine-2-carboxylic acid (3-phenylpropyl)amide as white crystals (0.116 g, 61% yield). MS (ES+) m/z 257.2 (M+1).

Workup

  1. stirringAfter stirring for 22 h
  2. washwashed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-a9fa6b3d185c4673b13359a4b947e175
Source dataset
uspto-grants-2013_02
Patent number
US08383628B2

Linked notes

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