Methylamine → HCID 86610020, compound

HRID 1712554Notes

Reaction equation

HRID 1712554 reaction equation
[CH3:1][NH2:2].[CH2:3]([N:5]([CH2:8][CH3:9])[CH2:6][CH3:7])[CH3:4].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl>[CH2:3]([N:5]1[CH2:8][CH2:9][CH:7]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([NH:2][CH3:1])=[O:17])[CH2:6]1)[C:4]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 86610020HCID 86610020, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.778 g of (R)-1-benzylpyrrolidin-3-yl)methylamine is dissolved in 20 ml of dichloromethane. 0.521 ml of triethylamine is added and the solution is cooled to 0° C. in an ice bath. 0.434 ml of benzoyl chloride is added dropwise and the reaction solution is subsequently stirred at 0° C. over 50 minutes. The reaction solution is diluted with 20 ml of dichloromethane and washed with 20 ml of saturated aqueous sodium hydrogencarbonate solution and 20 ml of brine, dried over sodium sulphate and concentrated by evaporation. The residue is purified by means of flash chromatography (SiO2 60F). The title compound is obtained as a colourless oil. Rf=0.75 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=3.08

Workup

  1. washwashed with 20 ml of saturated aqueous sodium hydrogencarbonate solution and 20 ml of brine
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated by evaporation
  4. customThe residue is purified by means of flash chromatography (SiO2 60F)

Sources & evidence

ORD record
ord-4cc4b7da2e17410fb1f569cc2612ec30
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

Loading…