Benzoyl chloride, 3,4,5-trimethoxy- → HCID 20394292, compound

HRID 261502Notes

Reaction equation

HRID 261502 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[O:7]2)[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[C:25](Cl)=[O:26]>C(Cl)(Cl)Cl>[CH3:34][O:33][C:29]1[CH:28]=[C:24]([CH:23]=[C:22]([O:21][CH3:20])[C:30]=1[O:31][CH3:32])[C:25]([N:1]1[CH2:6][CH2:5][C:4]2([CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[O:7]2)[CH2:3][CH2:2]1)=[O:26]

Participants

5

Reactant 3

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516892Sodium BicarbonateHCID 127332303H-Spiro(1-benzofuran-2,4'-piperidine)

Product 1

HCID 20394292HCID 20394292, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A stirred mixture of 5.0 g of 2,3-dihydrospiro[benzofuran-2,4'-piperidine], Example 7, and 15 g of sodium bicarbonate in 75 ml of chloroform is treated with a mixture of 8.8 g of 3,4,5-trimethoxybenzoyl chloride in 125 ml of chloroform according to the procedure of Example 7 to provide a tan solid. The solid is sequentially recrystallized from ethyl alcohol, chromatographed through a silica gel column with a 2% methyl alcohol in chloroform eluant and recrystallized from ethyl alcohol to give the product, 2,3-dihydro-1'-(3,4,5-trimethoxybenzoyl)spiro[benzofuran-2,4'-piperidine], mp 148°-150° C.

Workup

  1. customto provide a tan solid
  2. customThe solid is sequentially recrystallized from ethyl alcohol
  3. customchromatographed through a silica gel column with a 2% methyl alcohol in chloroform eluant
  4. customrecrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-9859a69d84de4746bfaffc573c0dfa25
Source dataset
uspto-grants-1979_08
Patent number
US04166119

Reaction notes

Loading…