Aniline → HCID 67185307, compound

HRID 2391024Notes

Reaction equation

HRID 2391024 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:11][CH:10]1[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:11][CH:10]1[CH3:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 86638966Toluene-4-sulfonic acid 4-benzylamino-3-methyl-cyclohexylmethyl ester

Product 1

HCID 67185307HCID 67185307, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture comprising toluene-4-sulfonic acid 4-benzylamino-3-methyl-cyclohexylmethyl ester (350 mg, 0.90 mmol), aniline (126, mg, 1.35 mmol) and potassium carbonate (250 mg, 1.80 mmol) in MeCN (1 mL) is heated using microwave radiation at 180° C. for 1 hour. The reaction mixture is partitioned between DCM and water and passed through a phase separator. The solvent is removed in vacuo and purification of the crude residue by chromatography on silica eluting with iso-hexane: EtOAc (25:1 increasing to 10:1) affords the title compound. [MH+ 309.34].

Workup

  1. customat 180° C.
  2. customfor 1 hour
  3. customThe reaction mixture is partitioned between DCM and water
  4. customThe solvent is removed in vacuo and purification of the crude residue by chromatography on silica eluting with iso-hexane: EtOAc (25:1 increasing to 10:1)

Sources & evidence

ORD record
ord-e07479d815e6499a9a47c5ca3a8e493a
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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