Water → HCID 53648437, compound

HRID 1196075Notes

Reaction equation

HRID 1196075 reaction equation
[Br:1][CH2:2][CH2:3][C:4](Cl)=[O:5].[CH2:7]([NH2:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].N1C=CC=CC=1.O>ClCCl>[Br:1][CH2:2][CH2:3][C:4]([NH:15][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 8143OctylamineHCID 84944Propanoyl chloride, 3-bromo-

Product 1

HCID 53648437HCID 53648437, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

3-Bromopropionyl chloride (25.7 g) was dissolved in dichloromethane (150 ml), cooled to -10° and a solution of octylamine (20.7 g) in dichloromethane (50 ml) was added over 10 minutes at -10° to 0°. Pyridine (12.7 g) in dichloromethane (50 ml) was added to the white suspension at -10° to 0° giving an orange solution. After stirring for 1 hour at 0°, water (100 ml) was added, the phases separated and the aqueous phase extracted with dichloromethane (2×50 ml). The combined organic extracts were washed with dilute sodium hydroxide and water, dried over MgSO4, filtered through a bed of silica gel and evaporated to give 3-bromo-N-octylpropanamide as a colourless solid (21.49 g, 54%) (mp 48°-55°).

Workup

  1. temperaturecooled to -10°
  2. customgiving an orange solution
  3. customthe phases separated
  4. extractionthe aqueous phase extracted with dichloromethane (2×50 ml)
  5. washThe combined organic extracts were washed with dilute sodium hydroxide and water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered through a bed of silica gel
  8. customevaporated

Sources & evidence

ORD record
ord-b324f2bd697c489cb9beccbea99b39fc
Source dataset
uspto-grants-1992_05
Patent number
US05112922

Reaction notes

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