N-Benzylphenethylamine → HCID 22716818, compound

HRID 1583042Notes

Reaction equation

HRID 1583042 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.CS(O[CH2:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH:35]=[O:36])(=O)=O>CN(C)C=O>[C:42]1([CH2:41][O:40][C:39]2[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][C:32]=2[CH2:31][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 65055N-BenzylphenethylamineHCID 81531DiisopropylethylamineHCID 21957468[2-(Benzyloxy)-5-formylphenyl]methyl methanesulfonate

Product 1

HCID 22716818HCID 22716818, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-benzyl-N-(2-phenylethyl)amine (351 mg) and diisopropyl-ethylamine (145 mg) in dimethylformamide (1.5 ml) was added 3-[[(methylsulfonyl)oxy]methyl]-4-phenylmethoxybenzaldehyde (355 mg). After stirring at room temperature for 3 hours, the reaction mixture was partially concentrated under reduced pressure and the residue was purified by flash chromatography column using petroleum ether:diethyl ether (1:3) as eluant. The pure fractions were combined and evaporated under reduced pressure to give 4-phenylmethoxy-3-[[N-phenylmethyl-N-(2-phenylethyl)amino]methyl]benzaldehyde (420 mg) as a gum. 1H NMR (CDCl3) δ9.89 (s, 1H, CHO); 5.20 (s, 2H); 3.88 (s, 2H); 3.85 (s, 2H); 2.92 (m, 4H, CH2CH2).

Workup

  1. concentrationthe reaction mixture was partially concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography column
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d93e98fb43ab4ddeadcbf9f58ed91ebf
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

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