Isomethadol
Title: Isomethadol
CAS Registry Number: 25117-79-7
CAS Name: b-[2-(Dimethylamino)-1-methylethyl]-a-ethyl-b-phenylbenzeneethanol
Additional Names: 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
Molecular Formula: C21H29NO
Molecular Weight: 311.46
Percent Composition: C 80.98%, H 9.38%, N 4.50%, O 5.14%
Literature References: Prepn of a-dl-form by lithium aluminum hydride reduction of dl-isomethadone: May, Mosettig, J. Org. Chem. 13, 663 (1948). Prepn of a-isomers by lithium aluminum hydride reduction of the optical isomers and of b-isomers by sodium-propanol reduction: May, Eddy, ibid. 17, 1210 (1952). Stereochemistry of isomers: Portoghese, Williams, Tetrahedron Lett. 1966, 6299.
 
Derivative Type: b-dl-Form
Properties: Prisms from alcohol + water, mp 107-108.5°.
Melting point: mp 107-108.5°
 
Derivative Type: b-dl-Form hydrochloride
Properties: Crystals from alcohol + ether, mp 252-254°.
Melting point: mp 252-254°
 
Derivative Type: b-d-Form
Properties: Slim rods from alcohol + water, mp 94-95°; [a]D20 +13.3° (c = 1.65).
Melting point: mp 94-95°
Optical Rotation: [a]D20 +13.3° (c = 1.65)
 
Derivative Type: b-d-Form hydrochloride
Properties: Thin prisms from alcohol + ether, mp 241-243°; [a]D20 +13.5° (c = 1.78).
Melting point: mp 241-243°
Optical Rotation: [a]D20 +13.5° (c = 1.78)
 
Derivative Type: b-l-Form
Properties: mp 93.5-94.5°; [a]D20 -13.8° (c = 1.09).
Melting point: mp 93.5-94.5°
Optical Rotation: [a]D20 -13.8° (c = 1.09)
 
Derivative Type: b-l-Form hydrochloride
Properties: mp 241-243°; [a]D20 -13.5° (c = 1.56).
Melting point: mp 241-243°
Optical Rotation: [a]D20 -13.5° (c = 1.56)
 
Derivative Type: a-dl-Form
Properties: mp 100-102.5°.
Melting point: mp 100-102.5°
 
Derivative Type: a-dl-Form hydrochloride
Properties: mp 231-233° (sinters at 200°).
Melting point: mp 231-233° (sinters at 200°)
 
Derivative Type: a-d-Form
Properties: mp 124.5-125.5°; [a]D20 +19.1° (c = 0.63).
Melting point: mp 124.5-125.5°
Optical Rotation: [a]D20 +19.1° (c = 0.63)
 
Derivative Type: a-d-Form hydrochloride hemihydrate
Properties: mp 202-204°; [a]D20 +10.1° (c = 1.89).
Melting point: mp 202-204°
Optical Rotation: [a]D20 +10.1° (c = 1.89)
 
Derivative Type: a-l-Form
Properties: Prisms from alcohol + water, mp 125-126°; [a]D20 -19.7° (c = 1.43).
Melting point: mp 125-126°
Optical Rotation: [a]D20 -19.7° (c = 1.43)
 
Derivative Type: a-l-Form hydrochloride hemihydrate
Properties: Rectangular plates, mp 202-204°; [a]D20 -9.6° (c = 2.93).
Melting point: mp 202-204°
Optical Rotation: [a]D20 -9.6° (c = 2.93)
 
 
Status: This monograph has been retired and is no longer subject to revision or update.

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