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

HRID 245312Notes

Reaction equation

HRID 245312 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-]>[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 98.3%

Reagents, catalysts & solvents 1

HCID 5284359Calcium ChlorideCatalyst

Conditions

Temperature
33 °C

Procedure

Dibenzylamine (39.4 g, 0.20 mol) and calcium chloride (1 g, 9 mmol) were added to (S)-epichlorohydrin (185 g, 2 mol). The mixture was stirred at room temperature (33° C.) for 8 hours. Filtered, and the solvent was evaporated to provide 57 g of colorless oil in 97% yield.

Workup

  1. filtrationFiltered
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-86602fe82f0e4d8cb98ebfdb162b72bd
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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