Benzenemethanamine, 3-chloro- → 2-(3-Chloro-benzyl)-5-trifluoromethoxy-2,3-dihydro-isoindol-1-ylideneamine Hydrobromide

HRID 842934Notes

Reaction equation

HRID 842934 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].[Br:10][CH2:11][C:12]1[CH:19]=[C:18]([O:20][C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]>C(O)C>[BrH:10].[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:6]1[CH2:11][C:12]2[C:13](=[CH:16][CH:17]=[C:18]([O:20][C:21]([F:24])([F:22])[F:23])[CH:19]=2)[C:14]1=[NH:15]

Participants

4

Reactant 2

HCID 77802Benzenemethanamine, 3-chloro-HCID 226163012-(Bromomethyl)-4-(trifluoromethoxy)benzonitrile

Product 1

HCID 226163152-(3-Chloro-benzyl)-5-trifluoromethoxy-2,3-dihydro-isoindol-1-ylideneamine HydrobromideYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 3-chlorobenzylamine (62 mg, 0.442 mmol) in ethanol (500 μL) at 80° C. was added 2-bromomethyl-4-trifluoromethoxy-benzonitrile 16 (95 mg, 0.34 mmol) as a solution in ethanol (100 μL). After 30 min at 80° C., the ethanol was removed under reduced pressure, and the resulting residue was triturated with ether/ethanol to yield the title compound (colorless solid 90%). 1H NMR (400 MHz, CD3OD) δ8.48 (d, J=8.0 Hz, 1 H, Ar), 7.78 (s, 1 H, Ar), 7.71 (d, J=8.8 Hz, 1 H, Ar), 7.56 (s, 1 H, Ar), 7.45 (m, 2 H, Ar), 7.38 (m, 1 H, Ar), 5.12 (s, 2 H, CH2), 4.84 (s, 2 H, CH2); M/Z (ESI+) 341 ([M+H]+).

Workup

  1. customthe ethanol was removed under reduced pressure
  2. customthe resulting residue was triturated with ether/ethanol

Sources & evidence

ORD record
ord-5f6fedea83da4521a43adfc00163eb28
Source dataset
uspto-grants-2002_04
Patent number
US06376530B1

Reaction notes

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