Methylamine → {4-[(Methylamino)methyl]phenyl}(phenyl)methanone

HRID 435832Notes

Reaction equation

HRID 435832 reaction equation
[CH3:1][NH2:2].Br[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1>C1C=CC=CC=1>[C:11]([C:8]1[CH:9]=[CH:10][C:5]([CH2:4][NH:2][CH3:1])=[CH:6][CH:7]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 1229514-(Bromomethyl)benzophenone

Product 1

HCID 15334722{4-[(Methylamino)methyl]phenyl}(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 12.0 g. (0.379 mole) anhydrous methyl amine in 150 ml. benzene is treated dropwise with 34.8 g. (0.127 mole) α-bromo-p-benzoyl toluene in 300 ml. benzene for about 30 minutes. The resulting mixture is stirred for 4 hours at room temperature and the solvent removed in vacuo. The resulting residue is dissolved in ether and washed with water. The ether layer is then extracted three times with 2N hydrochloric acid and the acidic solution made basic by the addition of potassium hydroxide and extracted with ether. The ether layer is washed with water, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue is then chromatographed on silica gel to yield 4-benzoyl N-methyl benzyl amine (identified by spectral analysis).

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe resulting residue is dissolved in ether
  3. washwashed with water
  4. extractionThe ether layer is then extracted three times with 2N hydrochloric acid
  5. additionby the addition of potassium hydroxide
  6. extractionextracted with ether
  7. washThe ether layer is washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue is then chromatographed on silica gel

Sources & evidence

ORD record
ord-1fcf0d4ec13041f48604d3a8cee7ba53
Source dataset
uspto-grants-1977_02
Patent number
US04006248

Reaction notes

Loading…