1-Bromooctane → 1-(4-Tert-butylphenyl)-4-[4-(2,5-difluoro-4-methoxyphenyl)piperazin-1-yl]butan-1-one

HRID 269933Notes

Reaction equation

HRID 269933 reaction equation
C(OC1C=CC(N2CCNCC2)=CC=1F)C1C=CC=CC=1.C(Br)CCCCCCC.[F:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[C:35]([F:40])=[CH:34][C:33]=1[N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.[C:47]([C:51]1[CH:56]=[CH:55][C:54]([C:57](=[O:62])[CH2:58][CH2:59][CH2:60]Cl)=[CH:53][CH:52]=1)([CH3:50])([CH3:49])[CH3:48]>>[C:47]([C:51]1[CH:52]=[CH:53][C:54]([C:57](=[O:62])[CH2:58][CH2:59][CH2:60][N:44]2[CH2:45][CH2:46][N:41]([C:33]3[CH:34]=[C:35]([F:40])[C:36]([O:38][CH3:39])=[CH:37][C:32]=3[F:31])[CH2:42][CH2:43]2)=[CH:55][CH:56]=1)([CH3:50])([CH3:49])[CH3:48]

Participants

5

Reactant 4

HCID 81401-BromooctaneHCID 27236944'-tert-Butyl-4-chlorobutyrophenoneHCID 231114831-(4-Benzyloxy-3-fluorophenyl)piperazineHCID 231114921-(2,5-Difluoro-4-methoxyphenyl)piperazine

Product 1

HCID 231114101-(4-Tert-butylphenyl)-4-[4-(2,5-difluoro-4-methoxyphenyl)piperazin-1-yl]butan-1-oneYield 79.8%

Procedure

Production Example 38 was repeated except that 1-(4-benzyloxy-3-fluorophenyl)piperazine and n-octyl bromide were replaced with 1-(2,5-difluoro-4-methoxyphenyl)piperazine (228 mg) and 1-(4-tert-butylphenyl)-4-chlorobutan-1-one (239 mg). The resulting crude product was purified on silica gel column chromatography (eluent, ethyl acetate) to provide 1-(4-tert-butylphenyl)-4-[4-(2,5-difluoro-4-methoxyphenyl)piperazin-1-yl]-butan-1-one (343 mg).

Workup

  1. customThe resulting crude product was purified on silica gel column chromatography (eluent, ethyl acetate)

Sources & evidence

ORD record
ord-3370eef1c60f41abbe0b2300cba1bfbe
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

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