Water → HCID 89581308, compound

HRID 2170509Notes

Reaction equation

HRID 2170509 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-c6468d6545484ababf5c896f61fd2114
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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