Hydrochloric Acid → 2-Methylspiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4'-piperidine]-6-carbonitrile dihydrochloride

HRID 1405345Notes

Reaction equation

HRID 1405345 reaction equation
[C:1]([C:3]1[N:7]2[CH2:8][CH2:9][N:10]([CH3:24])[C:11]3([CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[C:6]2=[CH:5][CH:4]=1)#[N:2].[ClH:25]>O1CCOCC1>[ClH:25].[ClH:25].[CH3:24][N:10]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:6]2=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[N:7]2[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68153526Tert-butyl 6-cyano-2-methyl-spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4'-piperidine]-1'-carboxylate

Product 1

HCID 681535912-Methylspiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4'-piperidine]-6-carbonitrile dihydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl 6-cyano-2-methyl-spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine]-1′-carboxylate (280 mg, 0.8474 mmol) was dissolved in a mixture of hydrochloric acid in dioxane (8 mL of 4 M, 32.00 mmol) and dioxane (8 mL). The reaction mixture was allowed to stir for 30 minutes and then evaporated to dryness to yield 2-methylspiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine]-6-carbonitrile dihydrochloride (258 mg, 99%) as a white solid. ESI-MS m/z calc. 230.2, found 231.5 (M+1)+; Retention time: 0.50 minutes (3 min run). 1H NMR (400 MHz, D2O) δ 7.10 (d, J=4.2 Hz, 1H), 6.59 (d, J=4.3 Hz, 1H), 4.51 (t, J=6.4 Hz, 2H), 4.02 (t, J=6.3 Hz, 2H), 3.66-3.56 (m, 2H), 3.49-3.36 (m, 2H), 2.95 (s, 3H), 2.69-2.59 (m, 2H), 2.54-2.40 (m, 2H).

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-182d7f13b4ae4f4eaa7a929bd28ed8e0
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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