Hydrochloric Acid → HCID 21937664, compound
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[NH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C.Cl>CN(C=O)C>[CH:20]1([CH2:19][NH:18][C:2]2[CH:7]=[CH:6][C:5]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][C:3]=2[N+:15]([O-:17])=[O:16])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1Participants
6
Procedure
A solution of 1-chloro-2-nitro-4-phenoxy-benzene (0.60 g, 2.58 mmol), (aminomethyl)cyclohexane (1.0 mL, 7.76 mmol) and N,N′-diisopropylethylamine (1.36, 7.76 mmol) in DMF (20.00 mL) was stirred at 100° C. under an inert atmosphere for 18.5 h. The reaction mixture was transferred to a separatory funnel containing HCl (2.0 N). The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water, brine and dried over MgSO4. The solution was filtered through diatomaceous earth and the solvent was evaporated. The resulting dark red residue was flash chromatographed (10% EtOAc/hexane) to give cyclohexylmethyl-(2-nitro-4-phenoxy-phenyl)-amine as a dark red solid (0.55 g, 65.6% yield).
Workup
- customThe reaction mixture was transferred to a separatory funnel
- extractionThe aqueous layer was extracted with EtOAc
- washthe combined organic layers were washed with water, brine
- dry with materialdried over MgSO4
- filtrationThe solution was filtered through diatomaceous earth
- customthe solvent was evaporated
- customchromatographed (10% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-68d50fd329664e7592593e61bde894de
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115644B2
Reaction notes
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