Methyl iodide → HCID 12289743, compound

HRID 2082762Notes

Reaction equation

HRID 2082762 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:6][CH2:7][NH:8][CH2:9][CH:10]([C:12]1[S:13][C:14]([CH3:17])=[CH:15][CH:16]=1)[OH:11].I[CH3:24]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:6][CH2:7][N:8]([CH2:9][CH:10]([C:12]1[S:13][C:14]([CH3:17])=[CH:15][CH:16]=1)[OH:11])[CH3:24]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 323804HCID 323804, compound

Product 1

HCID 12289743HCID 12289743, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of α-{[(3,4-dimethoxyphenethyl)amino]methyl}-5-methyl-2-thiophenemethanol (2.29 g, 0.007 mole), described in Example 16, and the lower alkyl halide, iodomethane (9.94 g, 0.07 mole), in 70 ml benzene is stirred at 25° C for 3 days. The mixture is concentrated under reduced pressure. The residual oil is taken up in methanol and made alkaline with 10% NaOH. The mixture is extracted wth chloroform. The extract is washed with water, dried (K2CO3) and concentrated to give a yellow oil, which is purified by chromatography to give the title compound; nmr (CDCl3) δ 2.41 (s, 3H), 2.46 (s, 3H), 2.6 - 2.8 (m, 6H), 3.68 (s, 1H), 3.83 (s, 3H), 3.88 (s, 3H), 4.88 (t, 1H), 6.6 - 6.9 (m, 5H).

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. extractionThe mixture is extracted wth chloroform
  3. washThe extract is washed with water
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated
  6. customto give a yellow oil, which
  7. customis purified by chromatography

Sources & evidence

ORD record
ord-ba693663e8404aff8a82d073e267ddbf
Source dataset
uspto-grants-1978_04
Patent number
US04082772

Reaction notes

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