4-Toluenesulfonyl chloride → 2-Nitro-4-piperidin-1-ylmethyl-benzoic acid methyl ester

HRID 1640969Notes

Reaction equation

HRID 1640969 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>ClCCl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8082PiperidineHCID 8471TriethylamineHCID 22672700Methyl 4-(hydroxymethyl)-2-nitrobenzoate

Product 1

HCID 667368402-Nitro-4-piperidin-1-ylmethyl-benzoic acid methyl esterYield 45.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxymethyl-2-nitro-benzoic acid methyl ester (2.0 g, 9.47 mmol) in dry dichloromethane (80 mL) under argon, at room temperature, triethylamine (1.6 mL, 10.9 mmol, 1.15 eq.) and then p-toluenesulfonyl chloride (2.08 g, 10.9 mmol, 1.15 eq.) were added. The reaction mixture was stirred at room temperature for 1 h, then piperidine (1.6 mL, 18.94 mmol, 2 eq.) was added and the mixture stirred for additional 24 hours. The solvent was evaporated and the residue purified by flash chromatography on silica gel, using dichloromethane/ethanol 95:5 as eluant, affording 1.2 g of the title compound.

Workup

  1. stirringthe mixture stirred for additional 24 hours
  2. customThe solvent was evaporated
  3. customthe residue purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-41dbc85d833e4ccf908f958ecae04f6b
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

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