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

HRID 245325Notes

Reaction equation

HRID 245325 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.[Cl-].[Li+].[CH2:18]([C@H:20]1[O:22][CH2:21]1)[Cl:19]>C1(C)C=CC=CC=1>[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

5

Reactant 3

HCID 7656DibenzylamineHCID 149428(+)-EpichlorohydrinHCID 433294Lithium Chloride

Product 1

HCID 49765557(S)-1-chloro-3-(dibenzylamino)propan-2-olYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

Dibenzylamine (39.4 g, 0.20 mol) and lithium chloride (12.6 g, 0.30 mol) were added to 100 mL of toluene. The mixture was stirred at 25° C. for 30 minutes. (S)-epichlorohydrin (18.6 g, 0.2 mol) was then added and stirred at 60° C. for 8 hours. The mixture was filtered and the solvent was evaporated to provide 52 g of colorless oil in 90% yield. HPLC: 99.3%.

Workup

  1. stirringstirred at 60° C. for 8 hours
  2. filtrationThe mixture was filtered
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a8bf5fbb548f44b8b99c7d322e8e0adb
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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