Dibenzylamine → (S)-1-chloro-3-(dibenzylamino)propan-2-ol

HRID 245308Notes

Reaction equation

HRID 245308 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([C@H:18]1[O:20][CH2:19]1)[Cl:17]>C(Cl)Cl>[Cl:17][CH2:16][C@@H:18]([OH:20])[CH2:19][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 149428(+)-Epichlorohydrin

Product 1

HCID 49765557(S)-1-chloro-3-(dibenzylamino)propan-2-olYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dibenzylamine (39.4 g, 0.20 mol) was added to 100 mL of methylene dichloride and stirred for 30 minutes. (S)-epichlorohydrin (21 g, 0.23 mol) was then added. The mixture was stirred at room temperature (25° C.) for 20 hours. Filtered, and the solvent was evaporated to provide 55 g of colorless oil in 93% yield.

Workup

  1. stirringThe mixture was stirred at room temperature (25° C.) for 20 hours
  2. filtrationFiltered
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cc1d1a70c1a9486b80c4e501192898b9
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

Loading…