Morpholine → HCID 16641133, compound

HRID 1637177Notes

Reaction equation

HRID 1637177 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]\[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[N+:17]([O-])=O.N1CCOCC1>C(O)C.CO.[Rh]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[NH2:17]

Participants

6

Reactant 2

HCID 8083MorpholineHCID 1712713HCID 1712713, compound

Product 1

HCID 16641133HCID 16641133, compoundYield 92.7%

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of the above nitrobenzene (9.68 g, 30.3 mmol) in ethanol (110 ml) and methanol (40 ml) was hydrogenated 2 h at 3 MPa in the presence of morpholine (0.6 ml) and Rh/C (KO 319) catalyst (2 g). The catalyst was filtered off, the filtrate evaporated in vacuo and the residue was stripped with toluene (3×20 ml). The oily residue crystallized after standing at room temperature. After washing the solid with petroleum ether and drying, 2-(2-(2-bromophenyl)ethyl)-5-methylaniline (8.15 g, 92%) was obtained.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated in vacuo
  3. customThe oily residue crystallized
  4. customafter standing at room temperature
  5. washAfter washing the solid with petroleum ether
  6. customdrying

Sources & evidence

ORD record
ord-b635689d0b43488b9b6086c09df8133d
Source dataset
uspto-grants-2000_03
Patent number
US06040302

Reaction notes

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