N-Methylbenzylamine → 5-[(Benzylmethylamino)methyl]-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one

HRID 2427506Notes

Reaction equation

HRID 2427506 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[C:8](=[O:13])[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[CH2:6]2.CN[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH:35]([N:38](C(C)C)CC)(C)C>C(#N)C>[CH2:28]([CH2:35][NH:38][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[C:8](=[O:13])[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[CH2:6]2)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 81531DiisopropylethylamineHCID 579495755-Bromomethyl-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one

Product 1

HCID 116624575-[(Benzylmethylamino)methyl]-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-oneYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 5-bromomethyl-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one (50 mg, 0.12 mmol) in acetonitrile (3 mL) was added drop wise to N-methylbenzylamine (24 mg, 0.2 mmol) and diisopropylethylamine (0.17 mL, 1 mmol) in acetonitrile (5 mL). After 4 hours the reaction was evaporated. The residue was chromatographed on silica gel, eluting with 0 to 25% ethyl acetate in methylene chloride, to give 45 mg (83% yield) of 5-[(benzylmethylamino)methyl]-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one as a colorless oil. 1H NMR (300.132 MHz, CDCl3) δ 7.37-7.28 (m, 6H), 7.25-7.14 (m, 5H), 4.75 (s, 2H), 4.21 (s, 2H), 3.53 (s, 2H), 3.52 (s, 2H), 2.74 (s, 3H), 2.18 (s, 3H).

Workup

  1. customAfter 4 hours the reaction was evaporated
  2. customThe residue was chromatographed on silica gel
  3. washeluting with 0 to 25% ethyl acetate in methylene chloride

Sources & evidence

ORD record
ord-405e7d0f34d041568e3518507383b78e
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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