Hydrochloric Acid → HCID 66600763, compound

HRID 2037494Notes

Reaction equation

HRID 2037494 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][CH2:11][CH2:12][C:13]2([CH:18]([CH3:20])[CH3:19])OCC[O:14]2)[CH3:9])=[CH:4][CH:3]=1.CO.Cl>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([NH:10][CH2:11][CH2:12][C:13](=[O:14])[CH:18]([CH3:20])[CH3:19])[CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66858173HCID 66858173, compound

Product 1

HCID 66600763HCID 66600763, compoundYield 82.2%

Conditions

Temperature
65 °C

Procedure

To a solution of [1-(4-bromo-phenyl)-ethyl]-[2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethyl]-amine (14.5 g, 0.042 mol) in MeOH (70 mol) was added HCl (36%, 70 mol). The mixture was stirred at 65° C. till the reaction was over. The mixture was cooled to 0° C. The pH of the mixture was adjusted to 7. The mixture was condensed, and the residue was extracted with EtOAc. The organic phase was dried over Na2SO4, and concentrated to give the crude 1-[1-(4-bromo-phenyl)-ethylamino]-4-methyl-pentan-3-one (10.3 g, crude), which was used for the next step without further purification. 1H NMR (CDCl3): 1.08 (m, 6H), 1.35 (m, 3H), 2.51-2.70 (m, 6H), 3.72 (m, 1H), 7.19 (m, 2H), 7.42 (m, 2H).

Workup

  1. temperatureThe mixture was cooled to 0° C
  2. customcondensed
  3. extractionthe residue was extracted with EtOAc
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2c273a9f82ce4391b3e9a6fe4fe390ad
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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