Isopropanol → alpha-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-1,1-dimethyl-ethyl]-aminomethyl]-benzyl alcohol
Reaction equation
[NH2:1][C:2]([CH3:16])([CH3:15])[CH2:3][O:4][C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1.[C:17]1([CH:23]2[CH2:25][O:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)(C)C>O1CCOCC1>[C:10]([C:9]1[CH:13]=[C:5]([CH:6]=[CH:7][C:8]=1[OH:14])[O:4][CH2:3][C:2]([NH:1][CH2:25][CH:23]([OH:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH3:15])(=[O:11])[NH2:12]Participants
5
Procedure
A solution of 4.5 g of 5-(2-amino-2-methyl-propoxy)-salicylamide and 3.1 g of 2-phenyloxirane in 40 ml of dioxane is refluxed for 16 hours. The solvent is subsequently evaporated off under reduced pressure, and the residue is dissolved in 20 ml of 2N hydrochloric acid, and extracted with 50 ml of ether. The water phase is separated; it is rendered alkaline with concentrated ammonia, and the liberated base is extracted with 200 ml of ethyl acetate. Customary further processing yields a light-coloured foam, from which is obtained, by recrystallisation from isopropanol, α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-1,1-dimethyl-ethyl]-aminomethyl]-benzyl alcohol, m.p. 121°-123°. It forms a neutral fumarate, m.p. 209°-210° (from methanol).
Workup
- customThe solvent is subsequently evaporated off under reduced pressure
- dissolutionthe residue is dissolved in 20 ml of 2N hydrochloric acid
- extractionextracted with 50 ml of ether
- customThe water phase is separated
- extractionthe liberated base is extracted with 200 ml of ethyl acetate
- customCustomary further processing yields a light-coloured foam
Sources & evidence
- ORD record
- ord-9b886e1594624d82980d314f142ad3c6
- Source dataset
- uspto-grants-1984_07
- Patent number
- US04460580
Reaction notes
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