1,5-Dibromopentane → N-(5-Bromopentyl)phthalimide
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.[K]>>[Br:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:12]1[C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]2[C:8]1=[O:18]Participants
3
Procedure
As shown in the above Reaction Scheme 1, 1,5-dibromopentane is reacted with potassium phthalimide in a suitable solvent to give N-(5-bromopentyl)phthalimide (2). The compound (2) is reacted with pyrrolidine in the presence of potassium carbonate and sodium iodide to give N-(5-pyrrolidin-1-ylpentyl)phthalimide (3). The compound (3) is reacted with hydrazine to provide 5-(pyrrolidin-1-yl)pentylamine (4). The compound (4) is reacted with di-t-butyl dicarbonate to give t-butyl (5-pyrrolidin-1-ylpentyl) carbamate (5). Then, the compound (5) is reacted with lithium aluminum hydride in a suitable solvent to give N-methyl-N-[5-(pyrrolidin-1-yl)pentyl]amine (6).
Sources & evidence
- ORD record
- ord-555d2bc19bc0457b94c35a3e0da856ed
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168646B2
Reaction notes
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