2-Methylcinnamic aldehyde → 6-Chloro-4-[1-(2-methyl-3-phenyl-allyl)-piperidin-4-ylamino]-chromen-2-One

HRID 897198

Reaction equation

HRID 897198 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2[NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[CH3:20][C:21](=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:22]=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]([CH3:22])=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 75572-Methylcinnamic aldehydeHCID 116376956-Chloro-4-(piperidin-4-ylamino)chromen-2-one

Product 1

HCID 726236826-Chloro-4-[1-(2-methyl-3-phenyl-allyl)-piperidin-4-ylamino]-chromen-2-OneYield 25.8%

Procedure

According to Procedure A above, 6-chloro-4-(piperidin-4-ylamino)-chromen-2-one and 2-methyl-3-phenyl-propenal (0.031 g, 0.216 mmol) were allowed to react to give the title compound (0.008 g, 25.8%, mono-TFA salt) as a off-white solid. 1H NMR (400 MHz, DMSO) δ ppm 8.35 (d, J=3, 1H), 7.66 (dd, J=3, 9, 1H), 7.32-7.47 (m, 6H), 6.76 (br s, 1H), 5.46 (s, 1H), 3.94-3.99 (m, 1H), 3.86 (d, J=3, 9, 1H), 3.53-3.60 (m, 2H), 3.05-3.20 (m, 2H), 2.18-2.28 (m, 2H), 2.05-2.15 (m, 1H), 2.01 (s, 3H), 1.82-1.91 (m, 2H); MS (ESI+Q1MS) m/z 409 [M]+

Workup

  1. customto react

Sources & evidence

ORD record
ord-9c728a2690184aeba4791d637d5300b1
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Linked notes

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