Dipentylamine → HCID 22716789, compound

HRID 1583041Notes

Reaction equation

HRID 1583041 reaction equation
[CH2:1]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:2][CH2:3][CH2:4][CH3:5].CS(O[CH2:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:21]=[O:22])(=O)=O>CN(C)C=O>[CH2:7]([N:6]([CH2:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:21]=[O:22])[CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 16316DipentylamineHCID 21957468[2-(Benzyloxy)-5-formylphenyl]methyl methanesulfonate

Product 1

HCID 22716789HCID 22716789, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of dipentylamine (258 mg) and diiosopropylethylamine (212 mg) in dimethylformamide (2 ml) was added 3-[[(methylsulfonyl)oxy]methyl]-4-phenylmethoxybenzaldehyde (350 mg). After stirring at room temperature for 2 weeks, the reaction mixture was partially concentrated under reduced pressure and the residue was purified by flash column chromatography using petroleum ether:diethyl ether (1:3) as eluant. The pure fractions were combined and evaporated under reduced pressure to give 3-[(dipentylamino)methyl]-4-phenylmethoxybenzaldehyde (356 mg) as a gum. 1H NMR (CDCl3) δ9.90 (s, 1H, CHO); 5.15 (s, 2H); 3.70 (s, 2H); 2.50 (m, 4H); 1.55 (m, 4H); 1.30(m, 8H); 0.90 (t, 6H).

Workup

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

Sources & evidence

ORD record
ord-50b18c6692ed408188cd4e9bc27864b7
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

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