Dihydrocoumarin → N-[3-(dimethylamino)propyl]-3-(2-hydroxyphenyl)propanamide

HRID 1250760Notes

Reaction equation

[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].[O:8]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:9]1=[O:10]>>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH:6][C:9](=[O:10])[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=1[OH:8]

Participants

Reactant 2

HCID 660Dihydrocoumarin

HCID 7993N,N-Dimethyl-1,3-propanediamine

Product 1

HCID 15541838N-[3-(dimethylamino)propyl]-3-(2-hydroxyphenyl)propanamideYield 106%

Conditions

Temperature: 70 °C

Procedure

N,N-Dimethyl-1,3-propanediamine (1.40 g) was added to 3,4-dihydrocoumarine (2.01 g) and stirred for 0.5 hour at 70° C., thereby yielding the entitled compound (3.60 g) as white solid.

Sources & evidence

ORD record: ord-d3376012c5e942d5aedaf95744d29584
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06339154B1

Reaction notes

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