4-Methylmorpholine → Pyridine-2-carboxylic acid 4-hydroxymethyl-benzylamide

HRID 2308284Notes

Reaction equation

HRID 2308284 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.ON1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=N1.CN1CC[O:25]CC1.CCN=C=NCCCN(C)C.Cl>>[OH:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:1][C:20]([C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:25])=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6496943[4-(Aminomethyl)phenyl]methanol

Product 1

HCID 22601292Pyridine-2-carboxylic acid 4-hydroxymethyl-benzylamideYield 95%

Procedure

Using General Procedure F: Reaction of (4-aminomethyl-phenyl)-methanol (200 mg, 1.46 mmol, 1-hydroxybenzotriazole (218 mg, 1.61 mmol), 4-methyl morpholine (241 μL, 2.19 mmol), and EDCl (309 mg, 1.61 mmol) for 2 h at room temperature gave the title compound (335 mg, 95%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 4.67 (d, 2H, J=6.0 Hz), 4.69 (s, 2H), 7.36 (br s, 4H), 7.43-7.44 (m, 1H), 7.85-7.86 (m, 1H), 8.24 (d, 1H, J=9.0 Hz), 8.52 (br s, 1H), 8.52 (d, 1H, J=3.0 Hz). ES-MS m/z 243 (M+H).

Sources & evidence

ORD record
ord-5a4585a53312435aa88defc2671842d6
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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