Morpholine → Morpholino(4-nitro-3-(trifluoromethyl)phenyl)methanone

HRID 2199731Notes

Reaction equation

HRID 2199731 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14])([O-:3])=[O:2].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C1C=CN=CC=1)C>[O:20]1[CH2:21][CH2:22][N:17]([C:8]([C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([C:13]([F:16])([F:15])[F:14])[CH:6]=2)=[O:10])[CH2:18][CH2:19]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162177534-Nitro-3-(trifluoromethyl)benzoic acid

Product 1

HCID 68936908Morpholino(4-nitro-3-(trifluoromethyl)phenyl)methanone

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-nitro-3-trifluoromethylbenzoic acid (10 g), morpholine (3.7 g) in dichloromethane (300 mL) was added DMAP (5.2 g) and 1-ethyl-3-(3-(dimethylamino)propyl)-carbodiimide hydrochloride (12.3 g). The mixture was stirred at room temperature overnight, washed with 5% aqueous HCl, water and brine and concentrated.

Workup

  1. washwashed with 5% aqueous HCl, water and brine
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-60c489ad437e4408bd461a6737a2a645
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

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