Ethyl 4-piperidinecarboxylate → Ethyl 1-(2,5-difluoro-4-methoxyphenyl)piperidine-4-carboxylate

HRID 269919Notes

Reaction equation

HRID 269919 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.[NH:22]1[CH2:32][CH2:31][CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24][CH2:23]1>>[F:18][C:17]1[CH:16]=[C:15]([O:19][CH3:20])[C:14]([F:21])=[CH:13][C:12]=1[N:22]1[CH2:32][CH2:31][CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 6083154-Bromo-1-methoxy-2-methylbenzeneHCID 27249834-Bromo-2,5-difluoroanisole

Product 1

HCID 23111500Ethyl 1-(2,5-difluoro-4-methoxyphenyl)piperidine-4-carboxylate

Procedure

Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-(2-phenethyl)piperazine were replaced with 4-bromo-2,5-difluoroanisole (4.460 g) and ethyl isonipecotate (3.70 mL), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=6:1) to provide ethyl 1-(2,5-difluoro-4-methoxyphenyl)piperidine-4-carboxylate (2.465 g).

Workup

  1. customThe resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=6:1)

Sources & evidence

ORD record
ord-28ac4ce592de4f8db7fd76514c418040
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

Loading…