Benzoyl chloride → HCID 59260672, compound

HRID 643269Notes

Reaction equation

HRID 643269 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[CH2:20][C:19]3([CH3:22])[CH2:21][CH:15]2[CH2:16][C:17]([CH3:24])([CH3:23])[CH2:18]3)=[O:13])=[CH:8][CH:7]=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][N:5]([C:6]1[CH:7]=[CH:8][C:9]([C:12]([N:14]2[CH2:20][C:19]3([CH3:22])[CH2:21][CH:15]2[CH2:16][C:17]([CH3:24])([CH3:23])[CH2:18]3)=[O:13])=[CH:10][CH:11]=1)[C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 59260674HCID 59260674, compound

Product 1

HCID 59260672HCID 59260672, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [4-(2-methoxy-ethylamino)-phenyl]-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone (0.1 g, 0.303 mmol) and TEA (0.13 ml, 0.91 mmol) in dry THF (20 ml) was added dropwise benzoyl chloride (0.07 ml, 0.61 mmol). The mixture was stirred for 1 hr. and evaporated in vacuo. The residue was purified on column chromatography (silicagel) using EtOAc-Heptane (1:1) as eluent. Pure fractions were collected; the solvent evaporated in vacuo affording 90 mg (68%) of the title compound as an oil.

Workup

  1. customand evaporated in vacuo
  2. customThe residue was purified on column chromatography (silicagel)
  3. customPure fractions were collected
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-04f28e4e891741cea7b1d17a6a6459a3
Source dataset
uspto-grants-2010_04
Patent number
US07700583B2

Reaction notes

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