13-05202. Isomethadol [Archived]
Nomenclature
CAS number: 25117-79-7
β-[2-(Dimethylamino)-1-methylethyl]-α-ethyl-β-phenylbenzeneethanol; 6-(dimethylamino)-5-methyl-4,4-diphenyl-3-hexanol; 1-dimethylamino-2-methyl-3,3-diphenyl-4-hexanol; 3-hydroxy-4,4-diphenyl-4-methyl-5-dimethylaminohexane. C21H29NO; mol wt 311.46.
C 80.98%, H 9.38%, N 4.50%, O 5.14%.
Description and references
Prepn of α-dl-form by lithium aluminum hydride reduction of dl-isomethadone: May, Mosettig, J. Org. Chem. 13, 663 (1948). Prepn of α-isomers by lithium aluminum hydride reduction of the optical isomers and of β-isomers by sodium-propanol reduction: May, Eddy, ibid. 17, 1210 (1952). Stereochemistry of isomers: Portoghese, Williams, Tetrahedron Lett. 1966, 6299.
Derivative
β-dl-Form.Properties
Prisms from alcohol + water, mp 107-108.5°.Derivative
β-dl-Form hydrochloride.Properties
Crystals from alcohol + ether, mp 252-254°.Derivative
β-d-Form.Properties
Slim rods from alcohol + water, mp 94-95°; [α]D20 +13.3° (c = 1.65).Derivative
β-d-Form hydrochloride.Properties
Thin prisms from alcohol + ether, mp 241-243°; [α]D20 +13.5° (c = 1.78).Derivative
β-l-Form.Properties
mp 93.5-94.5°; [α]D20 13.8° (c = 1.09).Derivative
β-l-Form hydrochloride.Properties
mp 241-243°; [α]D20 13.5° (c = 1.56).Derivative
α-dl-Form.Properties
mp 100-102.5°.Derivative
α-dl-Form hydrochloride.Properties
mp 231-233° (sinters at 200°).Derivative
α-d-Form.Properties
mp 124.5-125.5°; [α]D20 +19.1° (c = 0.63).Derivative
α-d-Form hydrochloride hemihydrate.Properties
mp 202-204°; [α]D20 +10.1° (c = 1.89).Derivative
α-l-Form.Properties
Prisms from alcohol + water, mp 125-126°; [α]D20 19.7° (c = 1.43).Derivative
α-l-Form hydrochloride hemihydrate.Properties
Rectangular plates, mp 202-204°; [α]D20 9.6° (c = 2.93).Status
This monograph has been retired and is no longer subject to revision or update.