Tert-Butylamine → Spirendolol

Reaction equation

Cl[CH2:2][CH:3]([OH:21])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][C:9]1([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:10]2=[O:15].O1CC1COC1C=CC=C2C=1CC1(CCCCC1)C2=O.[C:42]([NH2:46])([CH3:45])([CH3:44])[CH3:43]>O1CCOCC1>[C:42]([NH:46][CH2:2][CH:3]([OH:21])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][C:9]1([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:10]2=[O:15])([CH3:45])([CH3:44])[CH3:43]

Participants

Procedure

7.5 g of a mixture of mainly 4'-(3-chloro-2-hydroxypropoxy)-spiro(cyclohexane-1,2'-indan)-1'-one and of 4'-(2,3-epoxypropoxy)-spiro(cyclohexane-1,2'-indan)-1'-one in 50 ml dioxane and 30 ml tert.-butylamine are heated at 130° for 20 hours in an autoclave, then cooled and partitioned between 2 N tartaric acid and ether. The aqueous phase is made alkaline and extracted with ether. The organic phases are evaporated to yield the title compound in free base form (M.Pt. 87°-88°) which is converted into the hydrogen maleate; M.Pt. 180°-181°, and hydrogen malonate M.Pt. 143°-145°.