2-Methoxyethylamine → HCID 20298862, compound

HRID 1448101Notes

Reaction equation

HRID 1448101 reaction equation
Cl.Cl.[C:3]1([CH:9]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20](OC)=[C:19]([N+:25]([O-:27])=[O:26])[CH:18]=3)[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:34][O:35][CH2:36][CH2:37][NH2:38]>O>[C:28]1([CH:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([NH:38][CH2:37][CH2:36][O:35][CH3:34])=[C:19]([N+:25]([O-:27])=[O:26])[CH:18]=3)[CH2:14][CH2:15]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 20298733HCID 20298733, compound

Product 1

HCID 20298862HCID 20298862, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 20.8 parts of 1-(diphenylmethyl)-4-(4-methoxy-3-nitrophenylmethyl)piperazine dihydrochloride in 50 parts of 2-methoxyethanamine is stirred and refluxed overnight. Water is added and the product is extracted with dichloromethane. The extract is dried, filtered and evaporated. The residue is purified twice by columnchromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 11.6 parts (51%) of 4-[4-(diphenylmethyl)-1-piperazinylmethyl]-N-(2-methoxyethyl)-2-nitrobenzenamine; mp. 97.2° C.

Workup

  1. temperaturerefluxed overnight
  2. extractionthe product is extracted with dichloromethane
  3. customThe extract is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified twice by columnchromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated

Sources & evidence

ORD record
ord-031cc96f54724e718325a268b6d41abd
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

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