(alphaS)-4-Bromo-alpha-methylbenzenemethanamine → 3-((S)-1-(4-bromophenyl)ethylamino)-1-(4-fluorophenyl)butan-1-one

HRID 2037462Notes

Reaction equation

HRID 2037462 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]=[CH:10][CH3:11])=[CH:4][CH:3]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([NH2:22])[CH3:21])=[CH:16][CH:15]=1>CCO>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([NH:22][CH:10]([CH3:11])[CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:12])[CH3:21])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 668564531-(4-Fluorophenyl)but-2-en-1-one

Product 1

HCID 581091753-((S)-1-(4-bromophenyl)ethylamino)-1-(4-fluorophenyl)butan-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(4-fluorophenyl)but-2-en-1-one (13 g, 79.2 mmol) in EtOH (150 mL) was added (S)-1-(4-bromophenyl)ethanamine (32 g, 158 mmol), and the resulting mixture was stirred overnight. The solvent was removed in vacuo to give the crude 3-((S)-1-(4-bromophenyl)ethylamino)-1-(4-fluorophenyl)butan-1-one which was used for the next step without purification.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-aa4fbd6224b34eb0bb39226ca16d97bb
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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