Triethylamine → 2-(3-Bromophenyl)N-(3-propoxybenzyl)acetamide

HRID 1666904Notes

Reaction equation

HRID 1666904 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][NH2:9])[CH2:2][CH3:3].[Br:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21](Cl)=[O:22])[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C>ClCCl.[Cl-].[Na+].O>[Br:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([NH:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[CH:6]=2)=[O:22])[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 7139476(3-Propoxyphenyl)methanamineHCID 13486899(3-Bromophenyl)acetyl chloride

Product 1

HCID 210714132-(3-Bromophenyl)N-(3-propoxybenzyl)acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Combine 3-propoxy-benzylamine in 50 mL of dichloromethane and add dropwise to a mixture of 3-bromophenylacetyl chloride (4.90 gm; 21.0 mmol) and triethylamine (3.60 gm; 35.9 mmol) in 250 mL of dichloromethane at 0° C. Allow the reaction to warm to room temperature and stir for 18 h. Pour the reaction into 100 mL of saturated brine, separate the layers and extract the aqueous layer with 100 ml of dichloromethane. Combine organic layers, wash with brine, dry (MgSO4), and concentrate. Purification by chromatography on silica gel with 40% EtOAc in hexanes gives the title compound.

Workup

  1. customthe reaction
  2. additionPour
  3. customseparate the layers
  4. extractionextract the aqueous layer with 100 ml of dichloromethane
  5. washCombine organic layers, wash with brine
  6. dry with materialdry (MgSO4)
  7. concentrationconcentrate
  8. customPurification by chromatography on silica gel with 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-04783a4714cb4e41810e460f045c4625
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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