2,2-Diethoxyethylamine → HCID 15035615, compound

HRID 1461407Notes

Reaction equation

HRID 1461407 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:31])OC4C=CC=CC=4)=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[CH2:32]([O:34][CH:35]([O:38][CH2:39]C)[CH2:36][NH2:37])C>O1CCOCC1>[CH3:32][O:34][CH:35]([O:38][CH3:39])[CH2:36][NH:37][C:23]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([N:13]2[CH2:12][CH2:11][N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=3)[CH2:15][CH2:14]2)=[CH:21][CH:20]=1)=[O:31]

Participants

4

Reactant 2

HCID 695242,2-DiethoxyethylamineHCID 86745313HCID 86745313, compound

Product 1

HCID 15035615HCID 15035615, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 10 parts of phenyl [4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]carbamate monohydrochloride (described in example XVII of U.S. Pat. No. 4,267,179), 3 parts of 2,2-diethoxy-ethanamine and 100 parts of 1,4-dioxane was stirred for 6 hours at reflux temperature. After cooling, the precipitate was filtered off, washed with 1,4-dioxane and purified by column chromatography (silica gel; CHCl3 /CH3OH 99:1). The eluent of the desired fraction was evaporated and the residue was crystallized from 1,4-dioxane, yielding 3.9 parts of N-(2,2-dimethoxyethyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]urea; mp. 225° C. (interm. 8).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered off
  4. washwashed with 1,4-dioxane
  5. custompurified by column chromatography (silica gel; CHCl3 /CH3OH 99:1)
  6. customThe eluent of the desired fraction was evaporated
  7. customthe residue was crystallized from 1,4-dioxane

Sources & evidence

ORD record
ord-cc609a42955b4380bb179f5c75a146a1
Source dataset
uspto-grants-1991_12
Patent number
US05075309

Reaction notes

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