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

HRID 3314Notes

Reaction equation

HRID 3314 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:15][CH2:14][CH2:13][N:12]2[CH2:11][CH2:10][CH2:9]3)[CH:5]=[N:6][CH:7]=1.CCOCC.[ClH:21]>C(Cl)Cl>[ClH:21].[Br:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:15][CH2:14][CH2:13][N:12]2[CH2:11][CH2:10][CH2:9]3)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 189347147a-(5-bromo-3-pyridinyl)-hexahydro-1H-pyrrolizine

Product 1

HCID 189347727a-(5-Bromo-3-pyridinyl)-hexahydro-1h-pyrrolizine hydrochloride salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7a-(5-bromo-3-pyridinyl)-hexahydro-1H-pyrrolizine (107 mg, 0.52 mmol, from step 16c) was dissolved in methylene chloride, and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was crystallized from MeOH/Et2O and dried to afford the title compound as an off-white powder (118 mg). mp 192°-194° C. 1H NMR D2O, 300 MHz) δ2.13-2.51 (m, 6H), 2.57-2.66 (m, 2H), 3.36-3.44 (m, 2H), 3.81-3.89(m, 2H), 8.22 (s, 1H), 8.65 (s, 1H), 8.72 (s, 1H); MS (CI/NH3) m/z: 267/269 (M+H)+. Anal. Calcd for C12 H15BrN2.HCl: C, 47.47; H, 5.31; N, 9.23. Found: C, 47.40; H, 5.22; N, 8.98.

Workup

  1. customThe solvent was removed
  2. customthe solid was crystallized from MeOH/Et2O
  3. customdried

Sources & evidence

ORD record
ord-a1d18582f0384a23a908dc1e462f1ea7
Source dataset
uspto-grants-1998_03
Patent number
US05733912

Reaction notes

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