Triethylamine → Methyl 2-(4-benzyl-2-((methylsulfonyloxy)methyl)piperazin-1-yl)-5-nitrobenzoate

HRID 80509Notes

Reaction equation

HRID 80509 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])[CH:10]([CH2:27][OH:28])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])[CH:10]([CH2:27][O:28][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66769628Methyl 2-(4-benzyl-2-(hydroxymethyl)piperazin-1-yl)-5-nitrobenzoate

Product 1

HCID 87142397Methyl 2-(4-benzyl-2-((methylsulfonyloxy)methyl)piperazin-1-yl)-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a vigorously stirred solution of Example 45E (1 g, 2.59 mmol) in dichloromethane (5.19 mL) was added triethylamine (0.542 mL, 3.89 mmol) and methanesulfonyl chloride (0.253 mL, 3.24 mmol). The reaction was stirred for 10 minutes and then quenched with brine, extracted twice with dichloromethane, dried over sodium sulfate, and the solvent was evaporated to afford the title compound. MS (ESI+) m/z 464.1 (M+H)+.

Workup

  1. customquenched with brine
  2. extractionextracted twice with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-198dfe0c7e354d60b65b65a59918a3e4
Source dataset
uspto-grants-2014_09
Patent number
US08846663B2

Reaction notes

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