Dimethylformamide → 4-Piperidinecarboxamide

HRID 412318Notes

Reaction equation

C(OC1C=CC=CC=1[C:15]1[N:20]=[C:19](OCC(N)=O)[C:18](C#N)=[C:17](S(C)=O)[CH:16]=1)C1C=CC=CC=1.C[N:32]([CH:34]=[O:35])C>>[NH:20]1[CH2:15][CH2:16][CH:17]([C:34]([NH2:32])=[O:35])[CH2:18][CH2:19]1

Participants

Reactant 2

HCID 6228Dimethylformamide

HCID 22258909HCID 22258909, compound

Product 1

HCID 37724-Piperidinecarboxamide

Procedure

A mixture of 2-{[6-[2-(benzyloxy)phenyl]-3-cyano-4-(methylsulfinyl)-2-pyridinyl]-oxy}acetamide (500 mg, 1.19 mmol), which was obtained in the step (4) of Example 34-1, and isonipecotamide (228 mg, 1.78 mmol) in DMF (2 mL) was stirred at 130° C. for 5 hrs. After cooled to room temperature, the mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 1-{2-(2-amino-2-oxoethoxy)-6-[2-(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-4-piperidinecarboxamide as a solid (485 mg, yield; 84%).

Sources & evidence

ORD record: ord-9cbcf1bf25d84e2ebc72f144a3e5de4c
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562811B1

Reaction notes

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