Ethanol → 3-(Morpholin-4-ylmethyl)-5-(trifluoromethyl)aniline

HRID 254941Notes

Reaction equation

HRID 254941 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1)[CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([O-])=O.C(O)C.O.NN>C1COCC1.[Ni]>[N:8]1([CH2:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:16]=[C:15]([C:17]([F:18])([F:20])[F:19])[CH:14]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 219550054-[3-Nitro-5-(trifluoromethyl)benzyl]morpholine

Product 1

HCID 219550073-(Morpholin-4-ylmethyl)-5-(trifluoromethyl)anilineYield 102.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-nitro-5-trifluoromethylbenzyl)morpholine (168 mg; 0.57 mmol) in THF:ethanol mixture (1:1) (30 mL) was added a catalytical amount of Raney-Nickel and hydrazine hydrate (4.0 mmol) and the mixture was stirred for 2 hours at ambient temperature, then filtered through a Celite/silical gel pad. The filtrate was evaporated to provide the title compound (152 mg, 98%), which was used in further reactions without purification.

Workup

  1. filtrationfiltered through a Celite/silical gel pad
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-240536e9945a4c41ba21fff60dde1a5c
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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