4-(3-((Tert-butyldimethylsilyloxy)methyl)-4-nitrophenyl)morpholine → 2-((Tert-butyldimethylsilyloxy)methyl)-4-morpholinoaniline

HRID 1487196Notes

Reaction equation

HRID 1487196 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:13]=[CH:14][C:15]=1[N+:16]([O-])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Ni]>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:13]=[CH:14][C:15]=1[NH2:16])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 866996854-(3-((Tert-butyldimethylsilyloxy)methyl)-4-nitrophenyl)morpholine

Product 1

HCID 866996862-((Tert-butyldimethylsilyloxy)methyl)-4-morpholinoanilineYield 95.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(3-((tert-butyldimethylsilyloxy)methyl)-4-nitrophenyl)morpholine (4.0 g, 0.11 mol), Raney Ni (1.0 g) in methanol (250 mL) was stirred under an atmosphere of hydrogenated (1.0 atm) at room temperature for 1 hour. The catalyst was removed by filtration and the filtrate was evaporated to give the product 2-((tert-butyldimethylsilyloxy)methyl)-4-morpholinoaniline (3.48 g, yield 95.1%). 1H NMR (400 MHz, CDCl3) δ ppm 6.72-6.76 (m, 2H), 6.62-6.64 (d, 1H, J=8.0 Hz), 4.66 (s, 2H), 3.92 (s, 2H), 3.84-3.86 (t, 4H, J=4.4 Hz), 3.00-3.03 (t, 4H, J=4.8 Hz), 0.90-0.91 (m, 9H), 0.08-0.09 (m, 6H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-5d70625ff9b14666b944584f48740ae2
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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