1-(4-Bromophenyl)ethylamine → HCID 66858173, compound

HRID 2037493Notes

Reaction equation

HRID 2037493 reaction equation
[CH:1]([C:4]1([CH2:9][CH2:10]OS(C)(=O)=O)[O:8][CH2:7][CH2:6][O:5]1)([CH3:3])[CH3:2].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=1>>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([NH:25][CH2:10][CH2:9][C:4]2([CH:1]([CH3:2])[CH3:3])[O:5][CH2:6][CH2:7][O:8]2)[CH3:24])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 911751-(4-Bromophenyl)ethylamineHCID 107051032-(2-Isopropyl-1,3-dioxolan-2-yl)ethyl methanesulfonate

Product 1

HCID 66858173HCID 66858173, compoundYield 80.3%

Procedure

To a solution of methanesulfonic acid 2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethyl ester (19 g, 0.08 mol) was added 1-(4-bromo-phenyl)-ethylamine (48 g, 0.24 mol). The mixture was refluxed overnight. The mixture was condensed to give the crude product, which was purified by column to give [1-(4-bromo-phenyl)-ethyl]-[2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethyl]-amine (22 g, crude). 1H NMR (CDCl3): 0.88 (m, 6H), 1.32 (m, 3H), 1.83 (m, 3H), 2.51 (m, 2H), 3.69 (m, 1H), 3.87 (m, 4H), 7.18 (m, 2H), 7.43 (m, 2H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customcondensed
  3. customto give the crude product, which
  4. customwas purified by column

Sources & evidence

ORD record
ord-10c730feaeb2453ba984afba7c69c3ca
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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