1,4-Dioxa-8-azaspiro(4.5)decane → 8-(2,5-Difluoro-4-methoxyphenyl)-1,4-dioxa-8-azaspiro[4,5]decane

HRID 269915Notes

Reaction equation

HRID 269915 reaction equation
BrC1C=CC(OC)=C(C)C=1.C(N1CCNCC1)CC1C=CC=CC=1.Br[C:26]1[C:31]([F:32])=[CH:30][C:29]([O:33][CH3:34])=[C:28]([F:35])[CH:27]=1.[O:36]1[C:40]2([CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[O:39][CH2:38][CH2:37]1>>[F:32][C:31]1[CH:30]=[C:29]([O:33][CH3:34])[C:28]([F:35])=[CH:27][C:26]=1[N:43]1[CH2:44][CH2:45][C:40]2([O:39][CH2:38][CH2:37][O:36]2)[CH2:41][CH2:42]1

Participants

5

Reactant 4

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 792141-PhenethylpiperazineHCID 6083154-Bromo-1-methoxy-2-methylbenzeneHCID 27249834-Bromo-2,5-difluoroanisole

Product 1

HCID 231114208-(2,5-Difluoro-4-methoxyphenyl)-1,4-dioxa-8-azaspiro[4,5]decaneYield 31.9%

Procedure

Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-phenethylpiperazine were replaced with 4-bromo-2,5-difluoroanisole (1.115 g) and 1,4-dioxa-8-azaspiro[4,5]-decane (859 mg), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=3:1) to provide 8-(2,5-difluoro-4-methoxyphenyl)-1,4-dioxa-8-azaspiro[4,5]decane (455 mg).

Workup

  1. customThe resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f2ca42d4abda4f47bba3145d78b86179
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

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