2-Methoxyethylamine → HCID 20298862, compound

HRID 1389314Notes

Reaction equation

HRID 1389314 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 column-chromatography 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 column-chromatography 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-96c238310082405fbf25fe198a8dbf2a
Source dataset
uspto-grants-1981_01
Patent number
US04243806

Reaction notes

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