Hydrochloric Acid → HCID 68153356, compound

HRID 1405343Notes

Reaction equation

[CH3:1][N:2]1[C:14]2([CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[C:6]2=[CH:7][CH:8]=[C:9]([C:10]([F:13])([F:12])[F:11])[N:5]2[CH2:4][CH2:3]1.O1CCOCC1.CO.[ClH:35]>>[ClH:35].[ClH:35].[CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[C:9]([C:10]([F:11])([F:12])[F:13])=[CH:8][CH:7]=[C:6]2[C:14]21[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 312751,4-Dioxane

HCID 68153221tert-Butyl 2'-methyl-6'-(trifluoromethyl)-3',4'-dihydro-2'H-spiro[piperidine-4,1'-pyrrolo[1,2-a]pyrazine]-1-carboxylate

Product 1

HCID 68153356HCID 68153356, compound

Procedure

tert-Butyl 2-methyl-6-(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine]-1′-carboxylate (7.8 g, 20.89 mmol) was stirred in 4M HCl in dioxane (26.10 mL of 4 M, 104.4 mmol) and methanol (22 mL) at room temperature for 1 h. The reaction mixture was evaporated to dryness and the residue was co-evaporated with 100 mL of MTBE to afford 2′-methyl-6′-(trifluoromethyl)-3′,4′-dihydro-2′H-spiro[piperidine-4,1′-pyrrolo[1,2-a]pyrazine]dihydrochloride as a yellow foam/solid (7.23 g, quantitative). ESI-MS m/z calc. 273.2, found 274.5 (M+1)+; Retention time: 0.44 minutes (3 min run).

Workup

customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record: ord-d3c52d7339e5461caf0471e1a7b71664
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916565B2

Reaction notes

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