Trimethylsilyldiazomethane → Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate

HRID 1911365Notes

Reaction equation

HRID 1911365 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1>C1(C)C=CC=CC=1.CO.C(Cl)Cl>[CH3:8][N:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([O:22][CH3:1])=[O:21])=[CH:18][CH:17]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 47697824-(4-Methyl-1-piperazinylmethyl)benzoic acid

Product 1

HCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoateYield 44.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (trimethylsilyl)diazomethane ((0.611 mL, 3.84 mmol) 2.0M in diethyl ether) was added dropwise to a stirred suspension of 4-((4-methylpiperazin-1-yl)methyl)benzoic acid (0.75 g, 3.20 mmol) in toluene (21 mL) and methanol (7 mL) over a period of 10 mins under nitrogen. The resulting suspension was stirred at room temperature for 3 h. A further aliquot of (trimethylsilyl)diazomethane (1.222 mL, 7.68 mmol) was added dropwise and the solution was stirred at room temperature for a further 18 h. The reaction mixture was evaporated to dryness to afford the crude product (0.723 g) as a white solid. This was taken up in DCM and the insolubles were filtered off. The filtrate was evaporated to dryness to afford the crude product. This was taken up in DCM again and more insolubles were filtered off to afford methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate (0.351 g, 44.2%), which was used without purification.

Workup

  1. stirringthe solution was stirred at room temperature for a further 18 h
  2. customThe reaction mixture was evaporated to dryness
  3. customto afford the crude product (0.723 g) as a white solid
  4. filtrationthe insolubles were filtered off
  5. customThe filtrate was evaporated to dryness
  6. customto afford the crude product
  7. filtrationmore insolubles were filtered off

Sources & evidence

ORD record
ord-18a94bced0844a5cb313d7c5a5d4e80f
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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