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

HRID 245309Notes

Reaction equation

HRID 245309 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]>[Cl-].[Ca+2].[Cl-].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

5

Reactant 2

HCID 7656DibenzylamineHCID 149428(+)-Epichlorohydrin

Product 1

HCID 49765557(S)-1-chloro-3-(dibenzylamino)propan-2-olYield 96.6%

Reagents, catalysts & solvents 2

HCID 5284359Calcium ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Dibenzylamine (39.4 g, 0.20 mol) and calcium chloride (1 g, 9 mmol) were 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 (30° C.) for 5 hours. Filtered, and the solvent was evaporated to provide 56 g of colorless oil in 95% yield.

Workup

  1. stirringThe mixture was stirred at room temperature (30° C.) for 5 hours
  2. filtrationFiltered
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8aca6300debe430697cad2858882a936
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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