Morpholine → HCID 178457843, compound

HRID 518738Notes

Reaction equation

HRID 518738 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>>[CH:18]([NH:17][C:15]([C@H:12]1[CH2:13][CH2:14][C@@H:9]([NH:8][C:6]2[CH:7]=[C:2]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:3]=[CH:4][C:5]=2[N+:21]([O-:23])=[O:22])[CH2:10][CH2:11]1)=[O:16])([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 178457829HCID 178457829, compound

Product 1

HCID 178457843HCID 178457843, compoundYield 110.2%

Procedure

A suspension of cis-4-(5-chloro-2-nitrophenylamino)-N-isopropylcyclohexanecarboxamide (300 mg, 0.883 mmol) in morpholine (2 mL, 22.93 mmol) was irradiated in a microwave reactor for 1 hour at 150° C. The reaction mixture was partitioned between water and DCM. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to a yellow oil. The residue was concentrated, adsorbed onto a plug of silica gel, and purified by column chromatography, eluting with 0-100% EtOAc in DCM, to provide cis-N-isopropyl-4-(5-morpholino-2-nitrophenylamino)cyclohexanecarboxamide as a yellow powder (0.38 g, 110% yield). MS, m/z (C20H30N4O4): calcd, 390.2. found, 390.9 [M+H].

Workup

  1. customwas irradiated in a microwave reactor for 1 hour at 150° C
  2. customThe reaction mixture was partitioned between water and DCM
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow oil
  6. concentrationThe residue was concentrated
  7. custompurified by column chromatography
  8. washeluting with 0-100% EtOAc in DCM

Sources & evidence

ORD record
ord-1e968586e9714ad4aab9f19f6f71a25b
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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