Diethanolamine → HCID 69083496, compound

HRID 2205581Notes

Reaction equation

HRID 2205581 reaction equation
F[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[NH:16]([CH2:20][CH2:21][OH:22])[CH2:17][CH2:18][OH:19]>>[OH:19][CH2:18][CH2:17][N:16]([CH2:20][CH2:21][OH:22])[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8113DiethanolamineHCID 676634-Fluorobenzophenone

Product 1

HCID 69083496HCID 69083496, compoundYield 91.1%

Conditions

Temperature
155 °C

Procedure

A 2000 mL two-neck flask was charged with 4-fluorobenzophenone (200.0 g; 1.00 mol) and diethanolamine (735.2 g; 7.00 mol). The flask was flushed with nitrogen, fitted with a reflux condenser and heated to 155° C. for 48 h under a gentle stream of nitrogen. Complete conversion of the starting 4-fluorobenzophenone was confirmed by TLC. After cooling to ambient temperature, the dark viscous reaction mass was diluted with ethyl acetate (2500 mL) and extracted with water (2000 mL). The organic phase was dried (MgSO4), filtered and evaporated to give {4-[bis(2-hydroxyethyl)amino]phenyl}(phenyl)methanone (bright yellow powder; 260 g; 91% yield).

Workup

  1. customThe flask was flushed with nitrogen
  2. customfitted with a reflux condenser
  3. temperatureAfter cooling to ambient temperature
  4. additionthe dark viscous reaction mass was diluted with ethyl acetate (2500 mL)
  5. extractionextracted with water (2000 mL)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-69136b8afff24eae8371274fca4e1ba9
Source dataset
uspto-grants-2016_06
Patent number
US09371308B2

Reaction notes

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