2-(4-Chlorophenyl)ethylamine → HCID 737426, compound

HRID 1927736Notes

Reaction equation

HRID 1927736 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:21]([F:20])=[CH:22][CH:23]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674302-(4-Chlorophenyl)ethylamineHCID 678794-Fluorobenzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 737426HCID 737426, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-chlorophenyl)ethanamine (0.321 ml, 2.27 mmol) was diluted with DCM (10 mL) followed by the addition of DIEA (d 0.742) (0.395 ml, 2.27 mmol) and 4-fluorobenzoyl chloride (0.231 ml, 1.89 mmol). After stirring for 30 minutes the reaction was loaded directly onto a biotage 40S cartridge and eluted with hexanes:ethyl acetate (2:1) to yield N-(4-chlorophenethyl)-4-fluorobenzamide (393 mg, 74.8% yield) as a white solid.

Workup

  1. washeluted with hexanes:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-8c161f094fdd42b8ac3a29a4a736ce6f
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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