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

HRID 245327Notes

Reaction equation

HRID 245327 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(#N)C>[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 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

Dibenzylamine (39.4 g, 0.20 mol) and ferric chloride (12.6 g. 0.30 mol) were added to 100 mL of acetonitrile. 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. Filtered and the solvent was evaporated to provide 55 g of colorless oil in 94% yield. HPLC: 98%.

Workup

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

Sources & evidence

ORD record
ord-32d89b4277e1457f985d1c0b2d1b2a94
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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