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

HRID 245310Notes

Reaction equation

HRID 245310 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]>C(OCC)(=O)C>[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 82050Lithium BromideHCID 149428(+)-Epichlorohydrin

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dibenzylamine (39.4 g, 0.20 mol) and lithium bromide (1.7 g, 20 mmol) were added to 100 mL ethyl acetate and stirred for 30 minutes. (S)-epichlorohydrin (21 g, 0.23 mol) was then added. The reaction went on at room temperature (32° C.) for 2 hours. Filtered, and the solvent was evaporated to provide 53 g of colorless oil with 90% yield.

Workup

  1. waitThe reaction went on at room temperature (32° C.) for 2 hours
  2. filtrationFiltered
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f9e816d885674896b9ae7efb9f83ef88
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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