Methylamine → 3-(3-Methylphenyl)propan-1-amine

HRID 36857Notes

Reaction equation

HRID 36857 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6]Br.[CH3:11][NH2:12]>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][CH2:11][NH2:12]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 5706841-(2-Bromoethyl)-3-methylbenzene

Product 1

HCID 126663883-(3-Methylphenyl)propan-1-amine

Conditions

Temperature
80 °C

Procedure

A mixture of 3-methylphenethyl bromide (2.22 g) and 33% ethanolic methylamine solution (30 ml) was heated in a bomb at 80° C. for 16 hours and evaporated. The residue was partitioned between water and dichloromethane and the organic layer dried over MgSO4 and evaporated. The residue was purified by 421 chromatography on silica using dichloromethane plus 0-10% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless oil, 0.44 g (27%), which was used directly in the preparation of Example 21 without characterisation.

Workup

  1. customevaporated
  2. customThe residue was partitioned between water and dichloromethane
  3. dry with materialthe organic layer dried over MgSO4
  4. customevaporated
  5. customThe residue was purified by 421 chromatography on silica
  6. customevaporated

Sources & evidence

ORD record
ord-cd4ffebc5eb1432b884179004729c712
Source dataset
uspto-grants-1995_05
Patent number
US05418229

Reaction notes

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