Lactic Acid → 2-((6-Chrysenylmethyl)amino)-2-methyl-1,3-propanediol lactate

HRID 2413549Notes

Reaction equation

HRID 2413549 reaction equation
[CH:1]1[C:18]2[CH:17]=[CH:16][C:15]3[C:6](=[CH:7][C:8]([CH2:19][NH:20][C:21]([CH3:26])([CH2:24][OH:25])[CH2:22][OH:23])=[C:9]4[C:14]=3[CH:13]=[CH:12][CH:11]=[CH:10]4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:27](O)(=[O:31])[CH:28]([CH3:30])[OH:29]>CO>[C:27]([O:25][CH2:24][C:21]([NH:20][CH2:19][C:8]1[CH:7]=[C:6]2[C:15](=[C:14]3[C:9]=1[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:16]=[CH:17][C:18]1[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=1)([CH3:26])[CH2:22][OH:23])(=[O:31])[CH:28]([CH3:30])[OH:29]

Participants

4

Reactant 2

HCID 612Lactic AcidHCID 57062Crisnatol

Product 1

HCID 545379402-((6-Chrysenylmethyl)amino)-2-methyl-1,3-propanediol lactateYield 44.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-((6-chrysenylmethyl)amino)-2-methyl-1,3-propanediol free base (1D) (3.45 g, 10 mmol) and lactic acid (Fisher Scientific Co., 711 Forbes Ave., Pittsburgh, PA, 15219, 85% liquid, 1.04 g, 10 mmol) in CH3OH (500 mL) was brought to reflux and filtered through a glass fritted funnel. The solvent was removed by rotary evaporation to give a crude white solid. This was crystallized (CH3OH/Et3O) 3× to give 1.84 g (42.2%) of 2-((6-chrysenylmethyl)amino)-2-methyl-1,3-propanediol lactate mp 163°-164°, (C, H, N).

Workup

  1. temperatureto reflux
  2. filtrationfiltered through a glass fritted funnel
  3. customThe solvent was removed by rotary evaporation
  4. customto give a crude white solid
  5. customThis was crystallized (CH3OH/Et3O) 3×

Sources & evidence

ORD record
ord-31ed9c80a4f84003a8fd85885d1f5966
Source dataset
uspto-grants-1988_01
Patent number
US04719046

Reaction notes

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