Formaldehyde → 5,11-Dihydro-11-[1-oxo-6-(1-piperidinyl)-4-hexynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 4174

Reaction equation

HRID 4174 reaction equation
[O:1]=[C:2]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11](=[O:18])[NH:10][C:9]2[CH:19]=[CH:20][CH:21]=[N:22][C:8]1=2)[CH2:3][CH2:4][C:5]#[CH:6].[CH2:23]=O.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>[Cu]Cl.O1CCOCC1>[O:1]=[C:2]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11](=[O:18])[NH:10][C:9]2[CH:19]=[CH:20][CH:21]=[N:22][C:8]1=2)[CH2:3][CH2:4][C:5]#[C:6][CH2:23][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 137291885,11-dihydro-11-[1-oxo-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 137291895,11-Dihydro-11-[1-oxo-6-(1-piperidinyl)-4-hexynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture consisting of 9.6 g (0.03 mol) of 5,11-dihydro-11-[1-oxo-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 1.08 g (0.036 mol) of paraformaldehyde, 3.06 g (0.036 mol) of piperidine, 0.2 g of copper(I) chloride and 150 ml of dioxan is refluxed for 1 hour. After the reaction has ended the insoluble constituents are filtered off and the filtrate is evaporated to dryness in vacuo. The crude product is purified by column chromatography on silica gel (mobile phase: ethyl acetate, ethyl acetate+10% methanol). After recrystallisation from ethyl acetate, 2.7 g (21% of theory) of the desired compound are obtained, m.p. 197° C.

Workup

  1. temperatureis refluxed for 1 hour
  2. filtrationare filtered off
  3. customthe filtrate is evaporated to dryness in vacuo
  4. customThe crude product is purified by column chromatography on silica gel (mobile phase: ethyl acetate, ethyl acetate+10% methanol)
  5. customAfter recrystallisation from ethyl acetate, 2.7 g (21% of theory) of the desired compound
  6. customare obtained

Sources & evidence

ORD record
ord-301ed65de99248bebe2bd6e6ac674570
Source dataset
uspto-grants-1988_02
Patent number
US04724236

Linked notes

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