Homoveratrylamine → HCID 13118519, compound

HRID 838883Notes

Reaction equation

HRID 838883 reaction equation
Br[CH2:2][CH:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)[OH:4].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:15][CH2:16][NH2:17].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:15][CH2:16][NH:17][CH2:2][CH:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)[OH:4]

Participants

5

Reactant 3

HCID 8421HomoveratrylamineHCID 14798Sodium HydroxideHCID 22324999HCID 22324999, compound

Product 1

HCID 13118519HCID 13118519, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the halohydrin, α-(bromomethyl)-2-thiophenemethanol (11.4 g, 0.055 mole), described in Example 4, and the primary amine, 3,4-dimethoxyphenethylamine (15 g, 0.083 mole), in 200 ml toluene is heated at reflux for 12 hr. The mixture is cooled to 25° C, shaken with 10% NaOH an the layers separated. The aqueous layer is extracted with chloroform and the combined organic phases washed with water and brine, dried (K2CO3) and concentrated. The resulting dark brown oil is purified by chromatography on silica gel to give the title compound as an oil; nmr (CDCl3) 2.9 (m, 6H), 3.45 (2H), 3.85 (s, 6H), 5.05 (m, 1H), 6.7 - 7.3 (m, 6H).

Workup

  1. temperatureat reflux for 12 hr
  2. customseparated
  3. extractionThe aqueous layer is extracted with chloroform
  4. washthe combined organic phases washed with water and brine
  5. dry with materialdried (K2CO3)
  6. concentrationconcentrated
  7. customThe resulting dark brown oil is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e9a6e94783a44409b9cc1128830fe058
Source dataset
uspto-grants-1978_06
Patent number
US04093628

Reaction notes

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