Methylamine → (3-Methoxy)-alpha-methyl-alpha-[(methylamino)methyl]benzene methanol

HRID 2198883Notes

Reaction equation

HRID 2198883 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH3:12])[CH2:11][O:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:13][NH2:14]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:12])([CH2:11][NH:14][CH3:13])[OH:10])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 6329Methylamine2×HCID 204969162-(3-Methoxyphenyl)-2-methyloxirane

Product 1

HCID 62773765(3-Methoxy)-alpha-methyl-alpha-[(methylamino)methyl]benzene methanol

Procedure

2-(3-Methoxyphenyl)-2-methyloxiran (34.0 g) was stirred with aqueous methylamine (100 ml, 33%) and alcoholic methylamine (200 ml, 33%) overnight at ambient temperature. The mixture was evaporated to an oil under reduced pressure, dissolved in hydrochloric acid (2 M) and extracted with toluene. After basifying the aqueous acid with sodium hydroxide (5 M) the basic oil was extracted with toluene and dried (MgSO4). The solvent was removed under reduced pressure to leave the title compound as an oil (27.7 g). The hydrochloride was formed in isopropyl alcohol-ethereal hydrogen chloride, m.p. 155°-156° C. (Found: C, 57.55; H, 8.3; N, 5.8% C11H17NO2HCl requires C, 57.0; H, 7.8; N, 6.0%.

Workup

  1. customThe mixture was evaporated to an oil under reduced pressure
  2. dissolutiondissolved in hydrochloric acid (2 M)
  3. extractionextracted with toluene
  4. extractionwas extracted with toluene
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-51f1fa9dfe4c4beaa34acf22188b01d7
Source dataset
uspto-grants-1982_11
Patent number
US04360519

Reaction notes

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