Dimethylamine → Ethyl N-(3,4-dichlorobenzyl)-4-dimethylaminomethyl-5-hydroxyindole-2-carboxylate

HRID 1166059Notes

Reaction equation

HRID 1166059 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[CH3:25][NH:26][CH3:27].[CH2:28]=O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH2:25][N:26]([CH3:28])[CH3:27])[C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 11233838Ethyl N-(3,4-dichlorobenzyl)-5-hydroxyindole-2-carboxylate

Product 1

HCID 22997276Ethyl N-(3,4-dichlorobenzyl)-4-dimethylaminomethyl-5-hydroxyindole-2-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl N-(3,4-dichlorobenzyl)-5-hydroxyindole-2-carboxylate (2.1 g) in ethanol (50 ml) was added successively aqueous dimetylamine (40%, 0.5 ml) and aqueous formaldehyde (0.5 ml). The solution was allowed to stand overnight and the resulting crystals filtered and dried in vacuo to give the product as pale yellow crystals (1.7 g, 70%); NMR δ(CD3SOCD3) 1.24 (t, 3H), 2.23 (s, 6H), 3.81 (s, 2H), 4.24 (q, 2H), 5.75 (s, 2H), 6.82 (d, 1H), 6.90 (dd, 1H), 7.30 (m, 3H), 7.50 (d, 1H); M/z (+) 423.421 (MH−), 378, 376.

Workup

  1. filtrationthe resulting crystals filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-6b6bc082c47f4a5ebf03a7817055d83d
Source dataset
uspto-grants-2003_09
Patent number
US06613760B1

Reaction notes

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