N-Methylaniline → HCID 57691800, compound

HRID 422268Notes

Reaction equation

HRID 422268 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9](O)(=[O:14])[CH2:10][CH2:11][C:12]#[CH:13].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:9](=[O:14])[CH2:10][CH2:11][C:12]#[CH:13]

Participants

6

Reactant 4

HCID 7515N-MethylanilineHCID 224644-Pentynoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57691800HCID 57691800, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-methylbenzenamine (110 mg, 1.02 mmol) in DCM (3 mL) was successively added at R.T. 4-pentynoic acid (100 mg, 1.02 mmol), HOBT (171 mg, 1.12 mmol) and EDCI.HCl (293 mg, 1.53 mmol). The reaction was stirred at RT. Overnight. The reaction was quenched with water. The organic layer was separated and washed with 1M NaHCO3 and water. The solvent was removed under reduced pressure to afford 150 mg N-methyl-N-phenylpent-4-ynamide (Yield: 78%) as an orange oil which can be used without further purification.

Workup

  1. customOvernight
  2. customThe reaction was quenched with water
  3. customThe organic layer was separated
  4. washwashed with 1M NaHCO3 and water
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7b6f4f2ddc7f4f059b7e59dc51cdfdea
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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