Nicotinic Acid → HCID 19023658, compound

HRID 1034183Notes

Reaction equation

[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]2)[CH2:3][CH2:2]1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26](O)=[O:27])[CH:21]=1.C(OC(Cl)=O)C(C)C>>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:26]([C:22]3[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=3)=[O:27])[CH2:15][CH2:14]2)[CH2:3][CH2:2]1

Participants

Reactant 3

HCID 938Nicotinic Acid

HCID 62365Isobutyl chloroformate

HCID 86166943HCID 86166943, compound

Product 1

HCID 19023658HCID 19023658, compoundYield 15%

Procedure

N-[1-[2-(3,4-dihydro-2H-1-benzopyran-4-yl)ethyl]-4-aminopiperidine was coupled to pyridine-3-carboxylic acid utilizing the isobutylchloroformate protocol described in Example 6. The resulting residue was further purified by chromatography on silica (eluant: chloroform/ethanol/ammonium hydroxide; 85/14/1) and crystallization from diethyl ether to afford the title compound (15% yield), mp=126°-8°, Anal: C22H27N3O2 0.25 H2O, Calc. C, 71.42; H, 7.49; N, 11.36; Found: C, 71.25; H, 7.50; N, 11.19.

Workup

customThe resulting residue was further purified by chromatography on silica (eluant: chloroform/ethanol/ammonium hydroxide; 85/14/1) and crystallization from diethyl ether

Sources & evidence

ORD record: ord-cf42e230243d43c9ada7d1d104435246
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05314895

Reaction notes

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