L-Tartaric acid → HCID 86748411, compound

HRID 1769807Notes

Reaction equation

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

Participants

Conditions

Temperature: 4 °C

Procedure

(±)-N,N-Diisopropyl-3-(2-hydroxyphenyl)-3-phenylpropylamine (31.1 g, 0.10 mol) is dissolved in 300 ml of ethanol. A solution of L(+)-tartaric acid (15.0 g, 0.10 mol) in 400 ml of ethanol is added. The mixture is heated a few minutes in a boiling water bath and seeded with crystals obtained by cooling and scratching a small sample of the main solution. The mixture is chilled at about 4° C. over-night whereupon the crystalline precipitate is filtered off, washed with cold ethanol and recrystallized repeatedly from ethanol. The pure (-)-N,N-diisopropyl-3-(2-hydroxyphenyl)-3-phenylpropylamine hydrogen L-(+)-tartrate thus obtained has [α]D20 -10.6° (c=5% in methanol). The free amine is obtained by alkalisation of an aqueous solution, extraction into ether, drying and evaporation of the solvent. Sticky oil, [α]D20 -5.4° (c=5% in methanol).

Workup

temperatureThe mixture is heated a few minutes in a boiling water bath
customobtained
temperatureby cooling
filtrationis filtered off
washwashed with cold ethanol
customrecrystallized repeatedly from ethanol

Sources & evidence

ORD record: ord-d110f8281e3647d3ba4da80d62fee738
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05382600

Reaction notes

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