2-Methoxybenzylamine → 3-(2-Methoxybenzylamino)-1,1-diphenylpropan-2-one

HRID 1006351

Reaction equation

HRID 1006351 reaction equation
Br[CH2:2][C:3](=[O:17])[CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH2:23].C(N(CC)C(C)C)(C)C>O1CCCC1>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH:23][CH2:2][C:3](=[O:17])[CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 812922-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 27946353-Bromo-1,1-diphenylacetone

Product 1

HCID 226745333-(2-Methoxybenzylamino)-1,1-diphenylpropan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-bromo-1,1-diphenyl-2-propanone (0.5 g) in tetrahydrofuran (10 ml) was added to a mixture of (2-methoxy-benzyl)amine (1.13 ml) and N,N-diisopropylethylamine (0.602 ml) in tetrahydrofuran (12 ml) over 0.5 hour at room temperature. After being stirred at room temperature for 1.5 hours, the mixture was concentrated under reduced pressure to half volume and the resulting mixture was poured into ice-water (10 ml) and extracted with ethyl acetate (10 ml×2). The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give 3-[(2-methoxybenzyl)amino]-1,1-diphenylpropan-2-one (483 mg) as a colourless syrup.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure to half volume
  2. additionthe resulting mixture was poured into ice-water (10 ml)
  3. extractionextracted with ethyl acetate (10 ml×2)
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ff9512c27996433e964c07318633b344
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Linked notes

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