Hydrochloric Acid → 7a-(5,6-Dichloro-3-pyridinyl)-hexahydro-1h-pyrrolizine hydrochloride salt

HRID 3291Notes

Reaction equation

HRID 3291 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:16][CH2:15][CH2:14][N:13]2[CH2:12][CH2:11][CH2:10]3)[CH:5]=[N:6][C:7]=1[Cl:8].Cl>CCOCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:16][CH2:15][CH2:14][N:13]2[CH2:12][CH2:11][CH2:10]3)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 189347577a-(5,6-Dichloro-3-pyridinyl)-hexahydro-1h-pyrrolizine

Product 1

HCID 189347567a-(5,6-Dichloro-3-pyridinyl)-hexahydro-1h-pyrrolizine hydrochloride saltYield 151.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

7a-(5,6-dichloro-3-pyridinyl)-hexahydro-1H-pyrrolizine (from step 8b, 128 mg, 0.50 mmol) was slurried in Et2O (8 mL), and Et2O saturated with HCl (g) added. The solvent was removed, and the solid was recrystallized from MeOH/Et2O to afford a white solid (111 mg, 75%). mp 215°-217° C. MS (CI/NH3) m/e: 257 (M+H)+. 1H NMR D2O, 300 MHz) δ2.12-2.50 (m, 6H), 2.54-2.65 (m, 2H), 3.35-3.43 (m, 2H), 3.79-3.88 (m, 2H), 8.21 (d, J=2.4 Hz, 1H), 8.47 (d, J=2.4 Hz, 1H). Anal. Calcd for C12H15C13N2 : C, 49.09; H, 5.15; N, 9.54. Found: C, 49.01; H, 5.15; N, 9.44.

Workup

  1. customThe solvent was removed
  2. customthe solid was recrystallized from MeOH/Et2O

Sources & evidence

ORD record
ord-ea4bec3ef5714df3ac618bb631d33e9f
Source dataset
uspto-grants-1998_03
Patent number
US05733912

Reaction notes

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