Pyridine → 2-Bromo-N-[2-(4-phenoxy-phenyl)-ethyl]-acetamide

HRID 1353265Notes

Reaction equation

HRID 1353265 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([CH2:12][CH2:13][NH2:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17][CH2:18][C:19](Br)=[O:20].N1C=CC=CC=1>C(Cl)Cl>[Br:17][CH2:18][C:19]([NH:14][CH2:13][CH2:12][C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:16][CH:15]=1)=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 1455354-Phenoxyphenethylamine

Product 1

HCID 211025562-Bromo-N-[2-(4-phenoxy-phenyl)-ethyl]-acetamideYield 43.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-phenoxyphenethylamine (213.28 amu, 2.5 g, 1 eq, 10.8 mmol, 1.09 g/mL, 2.3 mL) added to a 3-necked flask. Bromoacetyl bromide (201.86 amu, 1.1 eq, 11.8 mmol, 2.4 g, 2.317 g/mL, 1.03 mL), pyridine (79.10 amu, 5 eq, 4.27 g, 0.978 g/mL, 54 mmol, 4.4 mL) added along with 50 mL CH2Cl2. Reaction stirred for 2 hours at RT. CH2Cl2 removed and mixture taken up in 200 mL EtOAc. Organic layer washed with brine and water (200 mL each). Organics seperated, dried sodium sulfate, and rotovaped to give 1.56 g material. MS [EI+] 334 (M+H)+, MS [EI−] 332 (M−H)+

Workup

  1. customReaction
  2. customCH2Cl2 removed
  3. washOrganic layer washed with brine and water (200 mL each)

Sources & evidence

ORD record
ord-7ec398ee41d84aae90e2c13b25c7f69b
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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