Potassium Carbonate → HCID 59627242, compound

HRID 1523255Notes

Reaction equation

HRID 1523255 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:18][CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:18][CH2:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 702953-ChloropropiophenoneHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamine

Product 1

HCID 59627242HCID 59627242, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of (S)-1-(4-bromophenyl)ethanamine (100 g, 0.502 mol) and K2CO3 (138.8 g, 0.10 mol) in acetonitrile (1000 mL) was added a solution of 3-chloro-1-phenyl-propan-1-one (84.4 g, 0.502 mol) in acetonitrile (100 mL). The reaction mixture was stirred overnight. The solid was filtered, and the filtrate was concentrated to give crude (S)-3-(1-(4-bromo-phenyl)ethylamino)-1-phenylpropan-1-one (110 g, 66.2%), which was used in the next step without further purification.

Workup

  1. filtrationThe solid was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-32e4c1ba16a7405c8a328087adf03715
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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