Ethylamine → HCID 18465165, compound

HRID 1276605Notes

Reaction equation

HRID 1276605 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]=[C:14]3[CH:24]=[CH:25][S:26][C:13]=23)[CH2:8][CH2:7]1)=O)C.[CH2:27]([NH2:29])[CH3:28].[Na]>CO>[CH2:27]([NH:29][C:4]([CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:15]=[C:14]3[CH:24]=[CH:25][S:26][C:13]=23)[CH2:10][CH2:11]1)=[O:3])[CH3:28]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 5360545SodiumHCID 15488005HCID 15488005, compound

Product 1

HCID 18465165HCID 18465165, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(5-phenylthieno[3,2-b]pyridin-7-yl)-4-piperidinecarboxylic acid ethyl ester (50 mg, 0.14 mmole), ethylamine (2 mL), and a catalytic amount of sodium cynide in MeOH (10 mL) is heated in a sealed tube at 70° C. oil bath for 48 hours. The solvent is removed on rotary-evaporator. The resulting residue is purified on a preparative tlc plate to give N-Ethyl 1-(5-phenylthieno[3,2-b]pyridin-7-yl)-4-piperidinecarboxamide (20 mg, 39% yield) as a colorless oil. This material is dissolved in ethyl acetate (1 mL), diluted with HCl saturated ethyl acetate (2 mL), and concentrated to afford N-ethyl 1-(6-phenylthieno[2,3-b]pyridin-4-yl)-4-piperidinecarboxamide hydrochloride (compound 1, 26 mg ) as greasy oil. The salt is solidified with ether, collected by filtration, washed with ether, and dried in vacuo. m.p.>270° C. (dec).

Workup

  1. customThe solvent is removed on rotary-evaporator
  2. customThe resulting residue is purified on a preparative tlc plate

Sources & evidence

ORD record
ord-dd85efb355a949f493fed674886ec43b
Source dataset
uspto-grants-2000_12
Patent number
US06166203

Reaction notes

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