Aniline → HCID 67185307, compound

HRID 1914662Notes

Reaction equation

HRID 1914662 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-da30ff5c316c466fb5f73342ff17d2a1
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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