Morpholine → HCID 16641133, compound

HRID 612417Notes

Reaction equation

HRID 612417 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-9f8fc6a4434c409fa7079d58b5018ff4
Source dataset
uspto-grants-1999_12
Patent number
US06004961

Reaction notes

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