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Hydrochloric Acid → 2-(aminocarbonyl)-N-(4-(aminomethyl)-2,6-dichlorophenyl]-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazineacetamide

HRID 1073193
Notes
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Reaction equation

HRID 1073193 reaction equation
[NH2:1][C:2]([CH:4]1[CH2:9][N:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:7][CH2:6][N:5]1[CH2:29][C:30]([NH:32][C:33]1[C:38]([Cl:39])=[CH:37][C:36]([CH2:40][NH:41]C(=O)OC(C)(C)C)=[CH:35][C:34]=1[Cl:49])=[O:31])=[O:3].CO.Cl>CC(O)C>[NH2:1][C:2]([CH:4]1[CH2:9][N:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH2:7][CH2:6][N:5]1[CH2:29][C:30]([NH:32][C:33]1[C:38]([Cl:39])=[CH:37][C:36]([CH2:40][NH2:41])=[CH:35][C:34]=1[Cl:49])=[O:31])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14722567(1,1-Dimethylethyl) [[4-[[2-[2-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazinyl]acetyl]amino]-3,5-dichlorophenyl]methyl]carbamate

Product 1

HCID 147226602-(aminocarbonyl)-N-(4-(aminomethyl)-2,6-dichlorophenyl]-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazineacetamideYield 44.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 8.7 parts of (1,1-dimethylethyl) [[4-[[2-[2-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazinyl]acetyl]amino]-3,5-dichlorophenyl]methyl]carbamate, 120 parts of methanol and 24 parts of 2-propanol, saturated with hydrogen chloride was stirred for 30 minutes at reflux temperature. The reaction mixture was evaporated and the residue was taken up in water. The whole was treated with an ammonium hydroxide solution and the product was extracted twice with dichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (93:7 by volume) as eluent. The desired fraction was collected and the eluent was evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.34 parts (44.9%) of 2-(aminocarbonyl)-N-(4-(aminomethyl)-2,6-dichlorophenyl]-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazineacetamide; mp. 160.8° C. (compound 100 ).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionThe whole was treated with an ammonium hydroxide solution
  4. extractionthe product was extracted twice with dichloromethane
  5. washThe combined extracts were washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol
  11. customThe desired fraction was collected
  12. customthe eluent was evaporated
  13. filtrationThe product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-99e254bfaeae4faebc1c293037d6200e
Source dataset
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04968684

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes