Hydrochloric Acid → Trifluoroacetic acid

HRID 2114518Notes

Reaction equation

HRID 2114518 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:27]3[CH:26]=[CH:25][C:24]([Cl:28])=[CH:23][C:22]=3[O:21][C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][C:19]=3[O:29][CH3:30])[CH2:10][CH2:9]1)=O)(C)(C)C.C(OC(N1CCC(N2C3C=CC(C4NN=NN=4)=CC=3OC3C2=CC=CC=3)CC1)=O)(C)(C)C.[C:63]([OH:69])([C:65]([F:68])([F:67])[F:66])=[O:64].Cl>C(Cl)Cl>[Cl:28][C:24]1[CH:25]=[CH:26][C:27]2[N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:15]3[C:20]([O:21][C:22]=2[CH:23]=1)=[C:19]([O:29][CH3:30])[CH:18]=[CH:17][CH:16]=3.[C:63]([OH:69])([C:65]([F:68])([F:67])[F:66])=[O:64]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 59809565HCID 59809565, compound2×HCID 178452046HCID 178452046, compound2×

Product 2

HCID 6422Trifluoroacetic acidHCID 11716943HCID 11716943, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using an adaptation of the method described in Procedure 6, substituting 4-(3-chloro-6-methoxy-phenoxazin-10-yl)-piperidine-1-carboxylic acid tert-butyl ester, 1p, for 4-[3-(1H-tetrazol-5-yl)-phenoxazin-10-yl]-piperidine-1-carboxylic acid tert-butyl ester, 5a, and a mixture of TFA in methylene chloride for a 4N hydrochloric acid solution, the title compound 3-chloro-6-methoxy-10-piperidin-4-yl-10H-phenoxazine, 7p was obtained as a TFA salt after purification via reverse phase HPLC (eluent gradient: CH3CN in water containing 0.1% TFA).

Sources & evidence

ORD record
ord-aab78a8dba124f64b64832190f00bee7
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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