Dimethylformamide → HCID 66989829, compound

HRID 454506Notes

Reaction equation

HRID 454506 reaction equation
CN(C)C=O.C(Cl)(=O)C(Cl)=O.[CH2:12]([O:19][C:20]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:25][C:21]=1[C:22]([OH:24])=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH2:35][C:36]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:37]=1[C:38]#[N:39]>C(Cl)Cl.N1C=CC=CC=1>[CH2:12]([O:19][C:20]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:25][C:21]=1[C:22]([NH:35][C:36]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:37]=1[C:38]#[N:39])=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 170059Benzonitrile, 2-amino-4-chloro-HCID 669910632-(Benzyloxy)-5-(piperidin-1-yl)benzoic acid

Product 1

HCID 66989829HCID 66989829, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

N,N-Dimethylformamide (0.010 mL) and oxalyl chloride (0.21 mL) were sequentially added to a methylene chloride (3.0 mL) suspension of 2-(benzyloxy)-5-(piperidin-1-yl)benzoic acid (0.56 g), followed by stirring at room temperature for 1 hour and 20 minutes. Under ice-cooling, the reaction mixture was added to a solution mixture of 2-amino-4-chlorobenzonitrile (0.23 g) in methylene chloride (3.0 mL) and pyridine (0.30 mL), followed by stirring at room temperature for 2 hours and 30 minutes. The solvent was evaporated under reduced pressure, and a 10% aqueous solution of citric acid and chloroform were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate] to obtain 2-(benzyloxy)-N-(5-chloro-2-cyanophenyl)-5-(piperidin-1-yl)benzamide as a yellow solid.

Workup

  1. temperatureUnder ice-cooling
  2. stirringby stirring at room temperature for 2 hours and 30 minutes
  3. customThe solvent was evaporated under reduced pressure
  4. additiona 10% aqueous solution of citric acid and chloroform were added to the residue
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-15796e1c5cae4f7a908f0f753e474ca6
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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