Dimethylformamide → HCID 19748235, compound

HRID 981605Notes

Reaction equation

HRID 981605 reaction equation
[N:1]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[O:21][CH2:22][CH2:23][CH2:24]Cl.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[ClH:12].[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[O:21][CH2:22][CH2:23][CH2:24][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 10340Sodium CarbonateHCID 14989174HCID 14989174, compound

Product 1

HCID 19748235HCID 19748235, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.16 parts of ethyl 1-piperazinecarboxylate, 4.7 parts of 2-chloro-1-(3-chloropropoxy)-4-methoxybenzene, 3.2 parts of sodium carbonate and 67.5 parts of N,N-dimethylformamide was stirred overnight at reflux temperature. After cooling, the reaction mixture was poured into water and the product was extracted with 2,2'-oxybispropane. The extract was dried, filtered and evaporated. The residue was converted into the hydrochloride salt in 2,2'-oxybispropane. The salt was filtered off and dried, yielding 4 parts (50%) of ethyl 4-[3-(2-chloro-4-methoxyphenoxy)propyl]-1-piperazinecarboxylate monohydrochloride (int. 12).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. extractionthe product was extracted with 2,2'-oxybispropane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe salt was filtered off
  8. customdried

Sources & evidence

ORD record
ord-273c52c0219a4fa2b24ea702a91750c0
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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