Dibenzylamine → (S)-[3-(N,N-Dibenzylamino)-2-hydroxypropoxy]-2-amino-3-nitrobenzene

HRID 1386898Notes

Reaction equation

HRID 1386898 reaction equation
[NH2:1][C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C@H:6]1[O:8][CH2:7]1.[CH2:16]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO>[CH2:24]([N:23]([CH2:7][C@H:6]([OH:8])[CH2:5][O:4][C:3]1[CH:9]=[CH:10][CH:11]=[C:12]([N+:13]([O-:15])=[O:14])[C:2]=1[NH2:1])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 15049327(S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane

Product 1

HCID 54232526(S)-[3-(N,N-Dibenzylamino)-2-hydroxypropoxy]-2-amino-3-nitrobenzeneYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane (8.0 g, 38.1 mmol) was dissolved in 250 mL of methanol and treated with dibenzylamine (8.05 mL, 42.0 mmol, d=1.026). The mixture was stirred at reflux for 10 hours and then cooled to 0° C. The resulting orange precipitate was filtered and washed with cold methanol, then dried to yield 12.1 g (78%) of a pale orange solid that was pure by NMR and TLC analysis. The material was used without further purification. NMR.

Workup

  1. temperatureat reflux for 10 hours
  2. filtrationThe resulting orange precipitate was filtered
  3. washwashed with cold methanol
  4. customdried

Sources & evidence

ORD record
ord-f91aee62ae1e44a79fc2adaeebe5e8c6
Source dataset
uspto-grants-2001_07
Patent number
US06265581B1

Reaction notes

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