Dimethylformamide → 4-Piperidinecarboxamide

HRID 1767402Notes

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-971fa7628bbb4306a0d9509431862800
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07232909B2

Reaction notes

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