Hydrochloric Acid → 4-[1-(4-Bromo-2,5-difluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid tert-butyl ester

HRID 2066901Notes

Reaction equation

HRID 2066901 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][N:15]=[C:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:22][C:23]1[CH:28]=[C:27]([F:29])[C:26](F)=[CH:25][C:24]=1[F:31].CCN(C(C)C)C(C)C.Cl>CS(C)=O.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][N:15]=[C:16]2[CH2:21][CH2:20][N:19]([C:26]3[CH:25]=[C:24]([F:31])[C:23]([Br:22])=[CH:28][C:27]=3[F:29])[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 675971-Bromo-2,4,5-trifluorobenzeneHCID 81531DiisopropylethylamineHCID 583335984-(Piperidin-4-ylideneaminooxy)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866550274-[1-(4-Bromo-2,5-difluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 69c (1.0 g, 3.4 mmol) and 1-bromo-2,4,5-trifluorobenzene were heated with iPr2NEt (1.7 mL, 10.2 mmol) in DMSO (5 mL) at 140° C. for 40 min 1M HCl and EtOAc were added and the organic phase dried over MgSO4 and concentrated. The mixture was purified by chromatography on silica gel eluting with EtOAc/Hexane to give 4-[1-(4-Bromo-2,5-difluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid tert-butyl ester 77a (720 mg).

Workup

  1. additionwere added
  2. dry with materialthe organic phase dried over MgSO4
  3. concentrationconcentrated
  4. customThe mixture was purified by chromatography on silica gel eluting with EtOAc/Hexane

Sources & evidence

ORD record
ord-7360e67f878a4b20bd5fda4c03fcba3f
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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