Acetic Acid → HCID 178501121, compound

HRID 538075Notes

Reaction equation

HRID 538075 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)[CH2:7][CH2:6]1)=[O:4].CC(O)=O.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH2:21])[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 178418361HCID 178418361, compoundHCID 178501122HCID 178501122, compound

Product 1

HCID 178501121HCID 178501121, compoundYield 169.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution 0.01 M of trans-4-{[2-(2-Nitro-phenyl)-ethylamino]-methyl}-cyclohexanecarboxylic acid methyl ester (2 g, 6.25 mmol) in MeOH (625 mL) with ˜1% of glacial AcOH (6.25 mL) was submitted to continuous flow rate hydrogenation by H-Cube (ThalesNano®) using a 10% Pd/C cartridge (small type cartridge, full hydrogen mode, flowrate of 1 mL/min). Finally, the solvent was removed under reduced pressure to obtain the titles compound (3.07 g, quantitative yield).

Workup

  1. customFinally, the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-50958466e0e64d57bd37f5e4b5f9f1d2
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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