Hydrochloric Acid → HCID 18934728, compound

HRID 3287Notes

Reaction equation

HRID 3287 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]23[CH2:15][CH2:14][CH2:13][N:12]2[CH2:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=1.Cl>CCOCC>[ClH:1].[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]23[CH2:15][CH2:14][CH2:13][N:12]2[CH2:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18934712HCID 18934712, compound

Product 1

HCID 18934728HCID 18934728, compoundYield 155.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

7a-(6-Chloro-3-pyridinyl)-hexahydro-1H-pyrrolizine (from step 5a, 210 mg, 0.94 mmol) was dissolved in Et2O (8 mL), and Et2O saturated with HCl (g) was added at ambient temperature. Solvent was then removed, and the remaining solid was recrystallized from MeOH/Et2O to afford short white needles (189 mg, 78%). mp 141°-143° C. MS (CI/NH3) m/e: 223 (M+H)+. 1H NMR D2O, 300 MHz) δ2.12-2.50 (m, 6H), 2.58-2.65 (m, 2H), 3.33-3.42 (m, 2H), 3.69-3.88 (m, 2H), 7.62 (d, J=8.5 Hz, 1HO, 7.99 (dd, J=8.5, 2.7 Hz, 1H), 8.53 (d, J=2.7 Hz, 1H). Anal. Calcd for C12H16Cl2N2 : C, 55.61; H, 6.22; N, 10.81. Found: C, 55.10; H, 6.36; N, 10.57.

Workup

  1. customSolvent was then removed
  2. customthe remaining solid was recrystallized from MeOH/Et2O

Sources & evidence

ORD record
ord-a738c3035f24486b85c6366c76778e5e
Source dataset
uspto-grants-1998_03
Patent number
US05733912

Reaction notes

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