Sodium Iodide → HCID 54174460, compound

HRID 1919545Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17].[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>>[N:18]1([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]2[C:11](=[O:12])[C:10]3=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]3[C:8]2=[O:17])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

Reactant 4

HCID 5238Sodium Iodide

HCID 11430Potassium Carbonate

HCID 31268Pyrrolidine

HCID 136770N-(5-Bromopentyl)phthalimide

Product 1

HCID 54174460HCID 54174460, compound

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-c24eaee2a98746d8b7596c23c021fd9d
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168646B2

Reaction notes

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