Piperazine → Methyl 3-piperazinovalerate

HRID 414363Notes

Reaction equation

[C:1]([O:7][CH3:8])(=[O:6])/[CH:2]=[CH:3]/[CH2:4][CH3:5].[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>>[N:9]1([CH:3]([CH2:4][CH3:5])[CH2:2][C:1]([O:7][CH3:8])=[O:6])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

Reactant 2

HCID 4837Piperazine

HCID 5364718Methyl 2-pentenoate

Product 1

HCID 20035198Methyl 3-piperazinovalerateYield 51.8%

Conditions

Temperature: 60 °C

Procedure

A mixture of 213 g of methyl 2-trans-pentenoate and 64 g of piperazine was stirred for 44 hours at 60° C. Fractional distillation gave 77.1 g of methyl 3-piperazinovalerate of boiling point 105° C./0.4 mbar, nD20 =1.4740, the yield being 51%, based on piperazine used. delta =0.70-1.80 (m, 5 H), 1.72 (s, 1 H), 2.0-3.2 (m, 11 H), 3.70 ppm (s, 3 H).

Workup

distillationFractional distillation

Sources & evidence

ORD record: ord-017697635df9482592b219a0c0269f5e
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04791220

Reaction notes

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