Cyclohexylamine → (4-(Cyclohexylamino)-3-nitrophenyl)methanol

HRID 2068301Notes

Reaction equation

HRID 2068301 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(N(CC)C(C)C)(C)C.[CH:22]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C)C=O.C(OCC)(=O)C>[CH:22]1([NH:28][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 41675874-Fluoro-3-nitrobenzyl alcohol

Product 1

HCID 46735182(4-(Cyclohexylamino)-3-nitrophenyl)methanol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (4-Fluoro-3-nitrophenyl)methanol (1.00 g, 0.0058 mol), N,N-diisopropylethylamine (2.036 mL, 0.0117) and cyclohexanamine (2.005 mL, 0.0175 mol) in N,N-Dimethylformamide (2.46 mL) was placed in a microwave vial, the contents were mixed thoroughly then microwaved at 130° C. for 7 minutes. The resultant gel was dissolved in ethyl acetate then washed with 5% citric acid, brine, dried and concentrated to give the title compound.

Workup

  1. additionthe contents were mixed thoroughly
  2. customthen microwaved at 130° C. for 7 minutes
  3. washthen washed with 5% citric acid, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-591b40c147fe40c99a99e425fad6502f
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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