Dimethylformamide → HCID 66917476, compound

HRID 1881713Notes

Reaction equation

[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C([NH:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(OC(C)(C)C)=O.C([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])C.[CH3:34][N:35](C=O)C>>[NH2:35][CH:34]1[CH2:31][CH2:30][N:29]([C:1]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([N:24]3[CH2:23][CH2:22][CH:21]([NH2:20])[CH2:26][CH2:25]3)=[O:7])=[CH:4][CH:3]=2)=[O:11])[CH2:32][CH2:33]1

Participants

Reactant 4

HCID 6228Dimethylformamide2×

HCID 7488Terephthaloyl chloride

HCID 8471Triethylamine

HCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 66917476HCID 66917476, compound

Procedure

Under an inert atmosphere of nitrogen a solution of terephthaloyl chloride (50.7 g, 0.249 mol) in DMF (200 mL) is added slowly to a mixture of 4-(N-Boc-amino)piperidine (100 g, 0.499 mol) and triethylamine (104 mL, 0.749 mol) in DMF (800 mL). The reaction mixture is allowed to stir at room temperature overnight. A white suspension forms and the resulting mixture is quenched slowly with saturated NaHCO3 solution (500 mL) and water (500 mL). The resulting suspension is stirred for 30 minutes and is filtered under vacuum to afford a white solid. The solid is dried under vacuum at 45° C. to yield the required product. [M+H]+ 531

Workup

customA white suspension forms and the resulting mixture is quenched slowly with saturated NaHCO3 solution (500 mL) and water (500 mL)
stirringThe resulting suspension is stirred for 30 minutes
filtrationis filtered under vacuum
customto afford a white solid
customThe solid is dried under vacuum at 45° C.

Sources & evidence

ORD record: ord-786fc0b108d14215858f57eee95b9bee
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318935B2

Reaction notes

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