Dimethylamine → Benzyl (E)-3-[3-(dimethylaminomethyl)-2-methyl-1H-indol-4-yl]-2-propenoate

HRID 1600177Notes

Reaction equation

HRID 1600177 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH:7]=[CH:6][CH:5]=2.[CH3:23][NH:24][CH3:25].[CH2:26]=O>C(O)(=O)C.O1CCCC1>[CH3:23][N:24]([CH2:26][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[NH:3][C:2]=1[CH3:1])[CH3:25]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 86752481Benzyl (E)-3-(2-methyl-1H-indol-4-yl)-2-propenoate

Product 1

HCID 86752485Benzyl (E)-3-[3-(dimethylaminomethyl)-2-methyl-1H-indol-4-yl]-2-propenoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Treatment of benzyl (E)-3-(2-methyl-1H-indol-4-yl)-2-propenoate (6.20 g) with dimethylamine (3.2 ml of 33% solution in methylated spirit), and formaldehyde (1.68 ml of 40% aqueous solution) in acetic acid (13 ml) and tetrahydrofuran (15 ml) according to the method of Preparation 12 gave thetitle compound as a foam (7.45 g), Rf. 0.3(SS3).

Sources & evidence

ORD record
ord-65d75357146440138172a093e1076941
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

Loading…