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

HRID 245322Notes

Reaction equation

HRID 245322 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]>[OH-].[Li+].CN(C)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 90%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Dibenzylamine (39.4 g, 0.20 mol) and lithium hydroxide (48 mg, 2 mmol) were added to 100 mL N,N-dimethyl formamide. The mixture was stirred at 25° C. for 30 minutes. (S)-epichlorohydrin (18.6 g, 0.2 mol) was then added and the mixture was stirred at 0° C. for 8 hours. The mixture was filtered and the solvent was evaporated to provide 52 g colorless oil with 90% yield. HPLC: 99.0%.

Workup

  1. stirringthe mixture was stirred at 0° C. for 8 hours
  2. filtrationThe mixture was filtered
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b38ae9f7c5b64cbfb86dfd453f3a556c
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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