4-Benzylpiperidine → 4-Benzyl-1-(2,5-difluoro-4-methoxyphenyl)piperidine

HRID 269909Notes

Reaction equation

HRID 269909 reaction equation
BrC1C=CC(OC)=C(C)C=1.Br[C:12]1[C:17]([F:18])=[CH:16][C:15]([O:19][CH3:20])=[C:14]([F:21])[CH:13]=1.C(N1CCNCC1)CC1C=CC=CC=1.[CH2:36]([CH:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[CH2:36]([CH:43]1[CH2:48][CH2:47][N:46]([C:12]2[CH:13]=[C:14]([F:21])[C:15]([O:19][CH3:20])=[CH:16][C:17]=2[F:18])[CH2:45][CH2:44]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 4

HCID 317384-BenzylpiperidineHCID 792141-PhenethylpiperazineHCID 6083154-Bromo-1-methoxy-2-methylbenzeneHCID 27249834-Bromo-2,5-difluoroanisole

Product 1

HCID 231114884-Benzyl-1-(2,5-difluoro-4-methoxyphenyl)piperidine

Procedure

Production Example 9 was repeated except that 5-bromo-2-methoxytoluene was replaced with 4-bromo-2,5-difluoroanisole (446 mg), and 1-phenethylpiperazine was replaced with 4-benzylpiperidine (2.30 mL). The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=4:1) to provide 4-benzyl-1-(2,5-difluoro-4-methoxyphenyl)piperidine (304 mg).

Workup

  1. customThe resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=4:1)

Sources & evidence

ORD record
ord-3987f2373a064c359b87bffb8d41cc42
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

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