2,3-Dihydroxybutanedioic Acid → HCID 19884951, compound

HRID 846203Notes

Reaction equation

HRID 846203 reaction equation
[CH3:1][N:2]([CH3:23])[CH:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:4][CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[C:24]([OH:33])(=[O:32])[CH:25]([CH:27]([C:29]([OH:31])=[O:30])[OH:28])[OH:26]>C(O)C.O>[C:29]([CH:27]([CH:25]([C:24]([OH:33])=[O:32])[OH:26])[OH:28])([OH:31])=[O:30].[CH3:23][N:2]([CH3:1])[CH:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:4][CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 6093437N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine

Product 1

HCID 19884951HCID 19884951, compoundYield 5.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine (32.44 g, 0.106 mol) was dissolved in 75 ml of ethanol and combined with 15.94 g (0.106 mol) of (+)-tartaric acid dissolved in 650 ml of water. The mixture was allowed to stand at room temperature overnight and the precipitated solid was vacuum filtered. The title compound (2.55 g) was isolated in enantiomerically pure form following seven recrystallizations from acetone. mp=94°-96° C.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-a358cccc7de04a65955c683a74643eb4
Source dataset
uspto-grants-1992_08
Patent number
US05135947

Reaction notes

Loading…