Ethyl 4-piperidinecarboxylate → 1-(4-Pyrimidinyl)-4-(ethoxycarbonyl)piperidine

HRID 2288720Notes

Reaction equation

HRID 2288720 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][N:4]=1.[NH:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1>>[N:6]1[CH:7]=[CH:8][C:3]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=1

Participants

3

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 219225564-Chloropyrimidine hydrochloride

Product 1

HCID 227219571-(4-Pyrimidinyl)-4-(ethoxycarbonyl)piperidineYield 46%

Procedure

4-Chloropyrimidine hydrochloride was reacted with ethyl piperidine-4-carboxylate to give ethyl 1-(4-pyrimidinyl)piperidine-4-carboxylate in 46% yield. A mixture of the material so obtained (0.5 g), 2N aqueous hydrochloric acid (5 ml) and THF (15 ml) was stirred and heated to reflux for 18 hours. The mixture was evaporated and the residue was washed with ethyl acetate. There was thus obtained 1-(4-pyrimidinyl)piperidine-4-carboxylic acid hydrochloride salt (0.49 g, 95%);

Sources & evidence

ORD record
ord-898d5a453c944cdc8d5ce938a58e53ac
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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