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Sodium Bicarbonate → Ethyl 4-[2-[1-(8-chloro-3-phthalazinyl)-4-piperidinyl]ethoxy]benzoate monohydrochloride

HRID 981651
Notes
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Reaction equation

HRID 981651 reaction equation
[Cl:1][N:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:12])=[CH:7][CH:8]=[CH:9]2)=[CH:4][NH:3]1.[NH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][O:21][C:22]2[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=2)[CH2:15][CH2:14]1.C(=O)([O-])O.[Na+]>C(O)C>[ClH:1].[Cl:12][C:6]1[C:5]2[C:10](=[CH:11][N:2]([N:13]3[CH2:14][CH2:15][CH:16]([CH2:19][CH2:20][O:21][C:22]4[CH:23]=[CH:24][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:31][CH:32]=4)[CH2:17][CH2:18]3)[NH:3][CH:4]=2)[CH:9]=[CH:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 14989200Ethyl 4-[2-(4-piperidinyl)ethoxy]benzoateHCID 197482793,8-Dichlorophthalazine

Product 1

HCID 19748240Ethyl 4-[2-[1-(8-chloro-3-phthalazinyl)-4-piperidinyl]ethoxy]benzoate monohydrochlorideYield 46.2%

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Procedure

A mixture of 4 parts of 3,8-dichlorophthalazine, 4.2 parts of ethyl 4-[2-(4-piperidinyl)ethoxy]benzoate, 4 parts of sodium hydrogen carbonate and 120 parts of ethanol was stirred and refluxed overnight. After evaporation, the residue was taken up in water and dichloromethane. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol. The salt was filtered off, washed with 2-propanol and 2,2'-oxybispropane and dried at 50° C., yielding 3.3 parts (46.2%) of ethyl 4-[2-[1-(8-chloro-3-phthalazinyl)-4-piperidinyl]ethoxy]benzoate monohydrochloride; mp. 172.4° C. (comp. 86).

Workup

  1. temperaturerefluxed overnight
  2. customAfter evaporation
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. washwashed with 2-propanol and 2,2'-oxybispropane
  11. customdried at 50° C.

Sources & evidence

ORD record
ord-e9468a5faf6e46d88623f809928e1063
Source dataset
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04992433

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes