Potassium Carbonate → HCID 59627231, compound

HRID 1523237Notes

Reaction equation

HRID 1523237 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][C:25]([F:28])=[CH:24][CH:23]=1)=[O:21]>CC#N>[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:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)=[O:21])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 676722-Chloro-4'-fluoropropiophenoneHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamine

Product 1

HCID 59627231HCID 59627231, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of (S)-1-(4-bromophenyl)ethanamine (20 g, 0.1 mol) and K2CO3 (28 g, 0.2 mol) in MeCN (200 mL) was added a solution of 3-chloro-1-(4-fluorophenyl)propan-1-one (18.6 g, 0.1 mol) in MeCN (20 mL). The mixture was stirred overnight. The solid was filtered, and the filtrate was concentrated to give (S)-3-(1-(4-bromophenyl)ethylamino)-1-(4-fluorophenyl)propan-1-one (30 g, 86%), which was used for the next step without purification. 1H NMR (CDCl3): δ=1.29 (m, 3H), 2.56-2.91 (m, 2H), 3.11 (m, 2H), 3.68 (q, 1H), 7.11 (m, 2H), 7.21 (m, 2H), 7.43 (m, 2H), 7.99 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-018d7fa267874dafbf9ca44386c924bc
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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