Water → HCID 89581308, compound

HRID 1479769Notes

Reaction equation

HRID 1479769 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:19])[CH2:16][CH2:17][NH2:18])=[CH:11][CH:10]=1.C(N(CC)CC)C.O>CN(C)C1C=CN=CC=1.ClCCl>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([CH3:19])[CH2:16][CH2:17][NH:18][C:5](=[O:7])[CH3:6])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 24260487HCID 24260487, compound

Product 1

HCID 89581308HCID 89581308, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

At 0° C., acetic anhydride (0.59 g, 5.75 mmol) was added dropwise into a mixture of 3-(4-bromophenyl)butan-1-amine (0.57 g, 2.5 mmol), triethylamine (1.16 g, 11.5 mmol) and 4-dimethylamino-pyridine (1.0 mg, 0.008 mmol) in anhydrous dichloromethane (10 mL) the mixture was stirred at room temperature for 1.5 hours, water (20 mL) was added and extracted with dichloromethane (10 mL×3), combined and concentrated the organic layers, the residue was purified by column chromatography (silica gel, dichloromethane/Methanol=50:1) to give N-(3-(4-bromophenyl)butyl)acetamide (0.66 g, 94.4%). LRMS (M+H+) m/z: calcd for 270.17. found 270.1.

Workup

  1. extractionextracted with dichloromethane (10 mL×3)
  2. concentrationconcentrated the organic layers
  3. customthe residue was purified by column chromatography (silica gel, dichloromethane/Methanol=50:1)

Sources & evidence

ORD record
ord-622430cab7034accb6bd79823fee7913
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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