Diethylamine → HCID 14897375, compound

HRID 2196177Notes

Reaction equation

HRID 2196177 reaction equation
[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13].CCN(C(C)C)C(C)C>ClCCl>[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([N:14]([CH2:15][CH3:16])[CH2:12][CH3:13])=[O:4]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 598182Bromophenylacetyl chloride

Product 1

HCID 14897375HCID 14897375, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Bromo-phenyl-acetyl chloride (191.0 mmol) was taken up in anhydrous dichloromethane (150 mL) and the resulting mixture was cooled to 0° C. in an ice bath. Diethylamine (14.1 g, 191 mmol) was then added drop-wise over 15 minutes, following which DIPEA (24.7 g, 191 mmol) was added over 5 minutes. The reaction mixture was stirred at ambient temperature for 4 h. The reaction mixture was then washed with water, dried over MgSO4, filtered and concentrated to yield a dark brown colored oil. The oil was purified by silica gel chromatography to yield the title compound as a yellow oil.

Workup

  1. additionwas added over 5 minutes
  2. washThe reaction mixture was then washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a dark brown colored oil
  7. customThe oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f6c7a83c561d4a24b21a5541eb98c988
Source dataset
uspto-grants-2012_12
Patent number
US08338426B2

Reaction notes

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