Hydrochloric Acid → 7a-(4-Methyl-3-pyridinyl)-hexahydro-1h-pyrrolizine dihydrochloride salt

HRID 3330Notes

Reaction equation

HRID 3330 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]12[CH2:15][CH2:14][CH2:13][N:12]1[CH2:11][CH2:10][CH2:9]2.[ClH:16]>CCOCC>[ClH:16].[ClH:16].[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]12[CH2:15][CH2:14][CH2:13][N:12]1[CH2:11][CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 189347417a-(4-methyl-3-pyridinyl)-hexahydro-1H-pyrrolizine

Product 1

HCID 189347407a-(4-Methyl-3-pyridinyl)-hexahydro-1h-pyrrolizine dihydrochloride saltYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

7a-(4-methyl-3-pyridinyl)-hexahydro-1H-pyrrolizine (37 mg, 0.18 mmol) was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was triturated with Et2O and dried to afford the title compound as a white solid (26.2 mg, 61%): mp 244°-247° C.; 1H NMR D2O, 300 MHz) δ2.01-2.16 (m, 2H), 2.27-2.52 (m, 4H), 2.65 (s, 3H), 2.65-2.78 (m, 2H), 3.45-3.54 (m, 2H), 3.87-3.96 (m, 2H), 7.75 (d, J=5.6 Hz, 1H), 8.49 (s, 1H), 8.55 (d, J=5.6 Hz, 1H); MS (CI/NH3): m/z 203 (M+H+). Anal. Calcd for C13H18N2.2 HCl: C, 56.73; H, 7.32; N, 10.18. Found: C, 56.94; H. 7.24; N, 9.99.

Workup

  1. customThe solvent was removed
  2. customthe solid was triturated with Et2O
  3. customdried

Sources & evidence

ORD record
ord-9f0d302e51834ee5ae59f2e30cfe7ffc
Source dataset
uspto-grants-1998_03
Patent number
US05733912

Reaction notes

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