Triethylamine → HCID 21905033, compound

HRID 1247322Notes

Reaction equation

HRID 1247322 reaction equation
Br[CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)=[O:4].Cl.[CH3:22][NH:23][CH3:24].C(N(CC)CC)C>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][NH:5][C:3](=[O:4])[CH:2]([N:23]([CH3:24])[CH3:22])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)#[N:14]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 10473Dimethylamine, hydrochloride2×HCID 21905686HCID 21905686, compound

Product 1

HCID 21905033HCID 21905033, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (RS)-2-bromo-N-(4-cyano-benzyl)-2-phenyl-acetamide (200 mg) in THF (10 ml) at rt under an Ar atmosphere were added dimethylamine, hydrochloride (149 mg), triethylamine (0.42 ml) and tetrabutylammonium iodide (34 mg). The reaction mixture was stirred for 19 hrs, then treated with additional dimethylamine, hydrochloride (149 mg) and triethylamine (0.42 ml). After another 8 hrs stirring at rt, the solids were filtered off and washed with EtOAc. The filtrate was washed with water and brine, dried over MgSO4 and concentrated. The product was isolated by chromatography (silica gel, gradient dichloromethane=>dichloromethane/MeOH 9:1) to give (RS)-N-(4-cyano-benzyl)-2-dimethylamino-2-phenyl-acetamide (165 mg). Orange solid. MS 294.3 ([M+H]+)

Workup

  1. stirringAfter another 8 hrs stirring at rt
  2. filtrationthe solids were filtered off
  3. washwashed with EtOAc
  4. washThe filtrate was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe product was isolated by chromatography (silica gel, gradient dichloromethane=>dichloromethane/MeOH 9:1)

Sources & evidence

ORD record
ord-4e22005afdde4cd0bf156f9f5e823f59
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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