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

HRID 245311Notes

Reaction equation

HRID 245311 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.[Br-].[Li+].[CH2:18]([C@H:20]1[O:22][CH2:21]1)[Cl:19]>>[Cl:19][CH2:18][C@@H:20]([OH:22])[CH2:21][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 3

HCID 7656DibenzylamineHCID 82050Lithium BromideHCID 149428(+)-Epichlorohydrin

Product 1

HCID 49765557(S)-1-chloro-3-(dibenzylamino)propan-2-olYield 91.4%

Conditions

Temperature
25 °C

Procedure

Dibenzylamine (39.4 g, 0.20 mol) and lithium bromide (1.7 g, 20 mmol) were added to (S)-epichlorohydrin (185 g, 2 mol). The mixture was stirred at room temperature (25° C.) for 2 hours, Filtered, and the solvent was evaporated to provide 53 g of colorless Oil in 90% yield.

Workup

  1. filtrationFiltered
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bc67d106fc274d61bdafe7d7a5e4cd11
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

Loading…