Methyl iodide → HCID 12289743, compound

HRID 838885Notes

Reaction equation

HRID 838885 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 with 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 with 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-7962bbae74f44a58a88e80b93d8c001c
Source dataset
uspto-grants-1978_06
Patent number
US04093628

Reaction notes

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