1-Bromopentane → Benzamide, 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-(pentyloxy)-, hydrochloride (1:1)
Reaction equation
[ClH:1].[C:2]([NH:6][CH2:7][CH:8]([C:10]1[CH:18]=[C:14]([C:15]([NH2:17])=[O:16])[C:13]([OH:19])=[CH:12][CH:11]=1)[OH:9])([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CN(C)C=O>[ClH:1].[C:2]([NH:6][CH2:7][CH:8]([C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:14]([CH:18]=1)[C:15]([NH2:17])=[O:16])[OH:9])([CH3:5])([CH3:3])[CH3:4]Participants
Procedure
A mixture of 5-(2-tert-butylamino-1-hydroxyethyl) salicylamide, hydrochloride (8.7 g) and anhydrous potassium carbonate (8.25 g) in dimethylformamide (100 ml) were heated at 100° for 1 hour. 1-Bromopentane (4.5 g) in dimethylformamide (25 ml) was added and the mixture was heated at 100° for a further 2 hours. The solvent was removed and the residue was partitioned between water and ethyl acetate. The dried (MgSO4) ethyl acetate solution was evaporated to yield a red oil which was chromatographed on alumina. Eluation with ethyl acetate gave the required benzamide which was obtained as a colourless oil which was converted into its hydrochloride (1.55 g) m.p. 162°-167°. Recrystallisation from ethyl acetate-methanol raised the m.p. to 169°-172°.
Workup
- temperaturewere heated at 100° for 1 hour
- temperaturethe mixture was heated at 100° for a further 2 hours
- customThe solvent was removed
- customthe residue was partitioned between water and ethyl acetate
- dry with materialThe dried (MgSO4) ethyl acetate solution
- customwas evaporated
- customto yield a red oil which
- customwas chromatographed on alumina
Sources & evidence
- ORD record
- ord-db7797e1d3474434a9b1aeb0a519ae66
- Source dataset
- uspto-grants-1976_12
- Patent number
- US04000193
Reaction notes
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