4-(Aminomethyl)piperidine → N-(4-piperidinylmethyl)-5-(4-fluorophenyl)thieno[3,2-b]pyridin-7-amine

HRID 843660Notes

Reaction equation

HRID 843660 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:5]=[C:4]2[CH:15]=[CH:16][S:17][C:3]=12.[NH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>>[NH:23]1[CH2:24][CH2:25][CH:20]([CH2:19][NH:18][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=3)[N:5]=[C:4]3[CH:15]=[CH:16][S:17][C:3]=23)[CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 235274-(Aminomethyl)piperidineHCID 154874327-Chloro-5-(4-fluorophenyl)thieno[3,2-b]pyridine

Product 1

HCID 15487433N-(4-piperidinylmethyl)-5-(4-fluorophenyl)thieno[3,2-b]pyridin-7-amineYield 19%

Procedure

A solution of 7-chloro-5-(4-fluorophenyl)thieno[3,2-b]pyridine (60 mg, 0.23 mmole) in 4-aminomethylpiperidine (1 mL) is heated at 160° C. oil bath under N2 for 4 hours. The reaction mixture is cooled to room temperature and purified on preperative tlc plate to give N-(4-piperidinylmethyl)-5-(4-fluorophenyl) thieno[3,2-b]pyridin-7-amine (15 mg, 19% yield) as a colorless oil. This material is dissolved in 1 mL ethyl acetate. Ethyl acetate saturated with HCl (2 mL) is added and then concentrated to afford N-(4-piperidinylmethyl)-5-(4-fluorophenyl) thieno[3,2-b]pyridin-7-amine dihydrochloride (compound 1) as a greasy oil. The salt is triturated with ether, collected by filtration, washed with ether and dried in vacuo, m.p. >260° C. (dec).

Workup

  1. custompurified on preperative tlc plate

Sources & evidence

ORD record
ord-29fbf47c813344d699741324db585331
Source dataset
uspto-grants-2002_04
Patent number
US06380209B1

Reaction notes

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