2-Pyrrolidin-1-ylmethyl-piperidine → 1-(Indene-1-carbonyl)-2-(pyrrolidin-1-ylmethyl)piperidine

HRID 326732Notes

Reaction equation

HRID 326732 reaction equation
[N:1]1([CH2:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][NH:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:13]1([C:22](Cl)=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1>C(N(CC)CC)C>[CH:13]1([C:22]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]2[CH2:6][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

Participants

4

Reactant 2

HCID 27605412-Pyrrolidin-1-ylmethyl-piperidineHCID 189150771H-Indene-1-carbonyl chloride

Product 1

HCID 189150461-(Indene-1-carbonyl)-2-(pyrrolidin-1-ylmethyl)piperidineYield 32.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

From 2.36 g of 2-(pyrrolidin-1-ylmethyl)piperidine. 2.5 g of indene-1-carbonyl chloride and 4.88 ml of triethylamine. 1.4 g of 1-(indene-1-carbonyl)-2-(pyrrolidin-1-ylmethyl)piperidine was obtained using a procedure similar to that in Example 2. In a mixed solvent to methanol, water and ethanol (2:1:1), this compound was catalytically reduced with 10% palladium on carbon. After completion of the reduction, the catalyst was filtered off. After evaporation of the solvent, the residue was treated with a 4N 1,4-dioxane solution of hydrogen chloride to obtain 1.05 g of the title compound, melting at 218°-221° C.

Sources & evidence

ORD record
ord-6cd615d1c8364f64afd0f52b3b22aee5
Source dataset
uspto-grants-1993_12
Patent number
US05270327

Reaction notes

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