2-(4-Chlorophenyl)ethylamine → N-[2-(4-chlorophenyl)ethyl]-2-(2-fluorophenyl)acetamide

HRID 842026

Reaction equation

HRID 842026 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([CH2:17][CH2:18][NH2:19])=[CH:15][CH:14]=1.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([CH2:17][CH2:18][NH:19][C:9](=[O:11])[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 674302-(4-Chlorophenyl)ethylamineHCID 67979Benzeneacetic acid, 2-fluoro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 7048972N-[2-(4-chlorophenyl)ethyl]-2-(2-fluorophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Fluorophenylacetic acid (17 mg, 0.11 mmole) and 4-chlorophenethylamine (15 mg, 0.1 mmole) were dissolved in 5 ml dichloromethane. To this was added catalytic 4-dimethylaminopyridine (DMAP) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 33 mg, 0.11 mmole). The resulting solution was stirred at room temperature overnight. The reaction was then worked up by washing sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride. The compound was then purified by flash chromatography on silica gel (40:1 CHCl3/MeOH). 1H NMR (300 Mhz, CDCl3) δ 7.31-6.92 (m, 8H), 5.48 (bs, 1H), 3.51 (s, 2H), 3.42 (m, 2H), 2.70 (m, 2H).

Workup

  1. washby washing sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride
  2. customThe compound was then purified by flash chromatography on silica gel (40:1 CHCl3/MeOH)

Sources & evidence

ORD record
ord-2e585d0eb83a448dab5d531839122b61
Source dataset
uspto-grants-2002_04
Patent number
US06372752B1

Linked notes

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