Trifluoroacetic acid → 4-[(4-Bromophenyl)thio]piperidine

HRID 2288725Notes

Reaction equation

FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:28]=[CH:27][C:12]([S:13][CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:11][CH:10]=1>ClCCl>[Br:8][C:9]1[CH:28]=[CH:27][C:12]([S:13][CH:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 5 °C

Procedure

Trifluoroacetic acid (7.5 ml) was added in portions to a stirred, ice-cooled solution of 4-(4-bromothiophenoxy)-1-t-butoxycarbonylpiperidine (2.6 g) in dry dichloromethane (5 ml) under an atmosphere of argon so that the temperature of the mixture was maintained between 5 and 10° C. The solution was stirred at 5° C. for 1 hour, then at ambient temperature for 2 hours. The solution was evaporated. The residual oil was treated with a saturated aqueous solution of sodium carbonate and extracted with ethyl acetate (3×70 ml). The ethyl acetate extracts were combined, dried (Na2SO4) and evaporated. The residue was purified by flash column chromatography on silica gel, using a mixture of 95:5:3, ethyl acetate:methanol:aqueous ammonia (density 0.88 g/cm3) as eluent, to give 4-(4-bromothiophenoxy)piperidine (1.9 g) as an off-white solid;

Workup

temperaturewas maintained between 5 and 10° C
waitat ambient temperature for 2 hours
customThe solution was evaporated
additionThe residual oil was treated with a saturated aqueous solution of sodium carbonate
extractionextracted with ethyl acetate (3×70 ml)
dry with materialdried (Na2SO4)
customevaporated
customThe residue was purified by flash column chromatography on silica gel
additiona mixture of 95:5:3, ethyl acetate

Sources & evidence

ORD record: ord-74a2b22ee88343418ee1f9f20023ed91
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06090813

Reaction notes

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