Hydrazine → 5-Pyrrolidinoamylamine

HRID 1919546Notes

Reaction equation

HRID 1919546 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]2C(=O)C3=CC=CC=C3C2=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.NN>>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 9321HydrazineHCID 54174460HCID 54174460, compound

Product 1

HCID 70191825-Pyrrolidinoamylamine

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-61f68ad119f142dda3abb8909b363687
Source dataset
uspto-grants-2012_05
Patent number
US08168646B2

Reaction notes

Loading…