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Triethylamine → 7-[5,5-bis(4-fluorophenyl)-4-pentenyl]hexahydro-3,3-dimethylimidazo[1,5-a]pyrazin-1(5H)-one

HRID 1073155
Notes
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Reaction equation

HRID 1073155 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH:5]=[C:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[CH3:21][C:22]1([CH3:32])[N:26]2[CH2:27][CH2:28][NH:29][CH2:30][CH:25]2[C:24](=[O:31])[NH:23]1.C(N(CC)CC)C>CN(C)C=O>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:5][CH2:4][CH2:3][CH2:2][N:29]2[CH2:28][CH2:27][N:26]3[C:22]([CH3:32])([CH3:21])[NH:23][C:24](=[O:31])[CH:25]3[CH2:30]2)=[CH:8][CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14230278hexahydro-3,3-dimethylimidazo(1,5-a)pyrazin-1(5H)-oneHCID 147225505-Bromo-1,1-bis-(4-fluorophenyl)pent-1-ene

Product 1

HCID 147225477-[5,5-bis(4-fluorophenyl)-4-pentenyl]hexahydro-3,3-dimethylimidazo[1,5-a]pyrazin-1(5H)-oneYield 94%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
70 °C

Procedure

A mixture of 51 parts of 1,1'-(5-bromo-1-penten-1-ylidene)bis[4-fluorobenzene], 25.4 parts of hexahydro-3,3-dimethylimidazo-[1,5-a]pyrazin-1(5H)-one, 35.5 parts of N,N-diethylethanamine and 270 parts of N,N-dimethylformamide was stirred overnight at 70° C. After evaporation, the residue was taken up in trichloromethane. The organic layer was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 60 parts (94.0%) of 7-[5,5-bis(4-fluorophenyl)-4-pentenyl]hexahydro-3,3-dimethylimidazo[1.5-a]pyrazin-1(5H)-one as a residue (int. 24).

Workup

  1. customAfter evaporation
  2. washThe organic layer was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated

Sources & evidence

ORD record
ord-696f5e407b23486c9def7e7e2329c693
Source dataset
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04968684

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes