Piperazine → 1-(4-Benzyloxy-3-fluorophenyl)piperazine

HRID 269900Notes

Reaction equation

HRID 269900 reaction equation
BrC1C=CC(OC)=C(C)C=1.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][C:20]=1[F:26])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>>[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:21][C:20]=1[F:26])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 4837PiperazineHCID 6083154-Bromo-1-methoxy-2-methylbenzeneHCID 187574911-(Benzyloxy)-4-bromo-2-fluorobenzene

Product 1

HCID 231114831-(4-Benzyloxy-3-fluorophenyl)piperazineYield 54.1%

Procedure

Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-(2-phenethyl)piperazine were replaced with 1-benzyloxy-4-bromo-2-fluorobenzene (6.742 g) and piperazine (12.404 g), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, chloroform: methanol=2:1) to provide 1-(4-benzyloxy-3-fluorophenyl)piperazine (3.716 g).

Workup

  1. customThe resulting crude product was purified on silica gel column chromatography (eluent, chloroform: methanol=2:1)

Sources & evidence

ORD record
ord-85b653a234ca4a8f98ef32221a83778e
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

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