Hydrochloric Acid → 8-Fluoro-2-methyl-6-(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4'-piperidine]dihydrochloride

HRID 1405362Notes

Reaction equation

HRID 1405362 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:24]([F:27])([F:26])[F:25])[N:5]2[CH2:22][CH2:21][N:20]([CH3:23])[C:7]3([CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]3)[C:6]=12.[ClH:28]>C(Cl)Cl.O1CCOCC1>[ClH:28].[ClH:28].[F:1][C:2]1[CH:3]=[C:4]([C:24]([F:26])([F:25])[F:27])[N:5]2[CH2:22][CH2:21][N:20]([CH3:23])[C:7]3([CH2:8][CH2:9][NH:10][CH2:11][CH2:12]3)[C:6]=12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68153554Tert-butyl 8-fluoro-2-methyl-6-(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4'-piperidine]-1'-carboxylate

Product 1

HCID 888502048-Fluoro-2-methyl-6-(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4'-piperidine]dihydrochlorideYield 99.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl 8-fluoro-2-methyl-6-(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine]-1′-carboxylate (310 mg, 0.80 mmol) in CH2Cl2 (2 mL) was added a solution of HCl (2.0 mL of 4 M, 8.0 mmol) in 1,4-dioxane. The reaction mixture was allowed to stir at room temperature for 1 hour. The volatiles were removed under reduced pressure providing 8-fluoro-2-methyl-6-(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine]dihydrochloride (290 mg, 99%) as a pink solid. ESI-MS m/z calc. 291.1, found 292.3 (M+1)+; Retention time: 0.75 minutes (3 minute run).

Workup

  1. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-dee00dbdcafe4111a0baa1ee0bde8f44
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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