Benzoyl chloride → HCID 68502342, compound

HRID 1176562Notes

Reaction equation

HRID 1176562 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10](CN)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([N:17](CC)CC)C.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:17]([CH3:15])[C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 15194231-[(3R)-1-Benzylpyrrolidin-3-yl]methanamine

Product 1

HCID 68502342HCID 68502342, 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-6b5be76cc81e4fa4afdcbd8d46d7b685
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

Loading…