Diisopropylethylamine → HCID 59643248, compound

HRID 2251475Notes

Reaction equation

HRID 2251475 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[F:27][C:28]([F:42])([F:41])[C:29]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][C:30]=1[CH2:31]Br>ClCCl>[F:27][C:28]([F:41])([F:42])[C:29]1[CH:36]=[C:35]([C:37]([F:40])([F:38])[F:39])[CH:34]=[CH:33][C:30]=1[CH2:31][NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5188712,4-Bis(trifluoromethyl)benzyl bromideHCID 21320401Methyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoate

Product 1

HCID 59643248HCID 59643248, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoate (Biochim. Biophys. Acta 1997, 1339 (2), 321–330) (2 g; 8.44 mmol) in dichloromethane (20 ml) was treated with DIEA (1.47 ml; 8.44 mmol) and 2,4-bis-trifluoromethyl-benzyl bromide (2.59 g; 8.44 mmol). After stirring at rt overnight, the reaction mixture was concentrated and partitioned between ethyl acetate and saturated Na2CO3 solution. The organic phase was washed with Na2CO3 solution and brine, dried over sodium sulfate and concentrated. Purification by flash chromatography on silica gel using an ethyl acetate-hexane mixture (10–50%) afforded the title compound (2.0 g; 51% yield).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and saturated Na2CO3 solution
  3. washThe organic phase was washed with Na2CO3 solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel using an ethyl acetate-hexane mixture (10–50%)

Sources & evidence

ORD record
ord-dbf12498bfc5464d97f156fbd8d71744
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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