3-(Dimethylamino)phenol → [4-(3-Bromo-4,5-dimethoxyphenyl)-2-morpholin-4-yl-chroman-7-yl]-dimethyl-amine

HRID 1453998Notes

Reaction equation

HRID 1453998 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=[O:15])[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].[CH3:16][N:17]([CH3:25])[C:18]1[CH:19]=[C:20](O)[CH:21]=[CH:22][CH:23]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:22](=[CH:23][C:18]([N:17]([CH3:25])[CH3:16])=[CH:19][CH:20]=3)[O:15][CH:14]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 74213-(Dimethylamino)phenolHCID 8083MorpholineHCID 858878623-(3-Bromo-4,5-dimethoxyphenyl)-propenal

Product 1

HCID 69005398[4-(3-Bromo-4,5-dimethoxyphenyl)-2-morpholin-4-yl-chroman-7-yl]-dimethyl-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the 3-(3-bromo-4,5-dimethoxy-phenyl)-propenal (200 mg; 0.74 mmol), 3-(dimethylamino)phenol (101 mg, 0.74 mmol) and morpholine (65 μl; 0.75 mmol) in dry methanol (5 ml) was refluxed for 2 h and stirred at room temperature for 16 h. The solvent was removed and the intermediate [4-(3-bromo-4,5-dimethoxy-phenyl)-2-morpholin-4-yl-chroman-7-yl]-dimethyl-amine was obtained (350 mg).

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-6e1827fa9fc144fab10a960a9568ed0e
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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