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

HRID 245323Notes

Reaction equation

HRID 245323 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-].[Zn+2].[Cl-].CS(C)=O>[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 92%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

Dibenzylamine (39.4 g, 0.20 mol) and zinc chloride (81.6 g, 0.6 mol) were added to 200 mL dimethyl sulfoxide. The mixture was stirred at 25° C. for 30 minutes. (S)-epichlorohydrin (37.2 g, 0.4 mol) was then added and reacted at 120° C. for 8 hours. The mixture was filtered and water was added to the filtrate. The filtrate was extracted with ethyl acetate for 3 times, and then the organic phases were combined, the solvent was evaporated to provide 53 g of colorless oil with 92% yield. HPLC: 99.0%.

Workup

  1. customreacted at 120° C. for 8 hours
  2. filtrationThe mixture was filtered
  3. additionwater was added to the filtrate
  4. extractionThe filtrate was extracted with ethyl acetate for 3 times
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a1df5d2ff4964d68b800ef090a241926
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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