Methyl iodide → HCID 20066611, compound

HRID 358763Notes

Reaction equation

HRID 358763 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:10][CH:9]1[CH2:28][OH:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30]I.[H-].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:10][CH:9]1[CH2:28][O:29][CH3:30])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10341501HCID 10341501, compound

Product 1

HCID 20066611HCID 20066611, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-tert-butoxycarbonyl-4-(3,4,5-trimethoxybenzoyl)piperazine-2-methanol (12.0 g), methyl iodide (21.3 g) and dimethyl formamide (50 ml) is added, under ice-cooling while stirring, in limited amounts, 60% sodium hydride (1.8 g). The mixture is stirred for 30 further minutes, and the reaction mixture is poured into ice-water, followed by extraction with ethyl acetate. The organic layer is dried and concentrated. The residue is purified by means of a silica gel column chromatography (eluent: dichloromethane-ethyl acetate=1:1) to afford 1-tert-butoxycarbonyl-2-methoxymethyl-4-(3,4,5-trimethoxybenzoyl)piperazine (12.5 g) as colorless crystals, m.p. 127° C.

Workup

  1. additionis added, under ice-
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. customThe residue is purified by means of a silica gel column chromatography (eluent: dichloromethane-ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d46838bef694427492676aeef88b41c0
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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