(3-Bromopropyl)benzene → HCID 22660964, compound

HRID 392833Notes

Reaction equation

HRID 392833 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][NH:7][C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8](=[O:10])[CH3:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 3532104N-(4-Fluorobenzyl)acetamide

Product 1

HCID 22660964HCID 22660964, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(4-fluoro-benzyl)-acetamide (697 mg, 4.17 mmol) was suspended in toluene and treated with 668 mg of 60% NaH (mineral oil) followed by (3-bromopropyl)-benzene (1.27 mL, 8.34 mmol) and the resulting mixture stirred overnight. The mixture was filtered and the solvent removed. The crude product was purified by preparative HPLC (C18, MeOH/H2O-0.1% TFA) to yield 221 mg (19% yield) N-(4-Fluoro-benzyl)-N-(3-phenyl-propyl)-acetamide. HRMS (M+H) calcd for C18H21FNO: 286.1607; found: 286.1603. 1H NMR and 13C NMR show a mixture of rotamers at room temperature. 1H NMR (500 MHz, CDCl3) δ: 1.89 (m), 2.11 (s), 2.16 (s), 2.60 (t, J=7), 3.19 (dd, J=8, 8), 3.41 (dd, J=8, 8), 4.46 (s), 4.54 (s), 6.96-7.32 (overlapping m). 13C NMR (125 MHz, CDCl3) δ: 20.67, 21.21, 28.71, 29.53, 32.77, 33.14, 46.21, 47.25, 48.04, 51.60, 115.48, 115.65, 115.95, 116.12, 116.22, 126.04, 126.44, 128.01, 128.07, 128.28, 128.46, 128.68, 129.94, 130.01, 131.57, 131.59, 132.61, 132.64, 140.32, 141.19, 158.96, 159.28, 161.32, 161.37, 163.28, 163.34, 172.14, 172.46.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent removed
  3. customThe crude product was purified by preparative HPLC (C18, MeOH/H2O-0.1% TFA)

Sources & evidence

ORD record
ord-8d8ba0c219c84f82a29d20f1fba75e26
Source dataset
uspto-grants-2004_10
Patent number
US06803378B2

Reaction notes

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