Hydrochloric Acid → HCID 18934765, compound

HRID 3285Notes

Reaction equation

HRID 3285 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]23[CH2:14][CH2:13][CH2:12][N:11]2[CH2:10][CH2:9][CH2:8]3)[CH:2]=1.CCOCC.[ClH:20]>C(Cl)Cl>[ClH:20].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 104199907a-(3-Pyridinyl)-hexahydro-1h-pyrrolizine

Product 1

HCID 18934765HCID 18934765, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7a-(3-pyridinyl)-hexahydro-1H-pyrrolizine (from step 3a, 125 mg, 0.66 mmol) was dissolved in CH2Cl2 (15 mL) and Et2O saturated with HCl (g) was added dropwise. The solvent was removed, and the remaining solid was triturated with CH2Cl2 (2×) to afford a hygroscopic yellow solid (140 mg, 81%). MS (CI/NH3) m/e: 189 (M+H)+. 1H NMR (D2O, 300 MHz) δ2.13-2.29 (m, 2H), 2.32-2.43 (m, 2H), 2.48-2.69 (m, 4H), 3.40-3.49 (m, 2H), 3.83-3.92 (m, 2H), 7.92 (dd, J=8.5, 5.5 Hz, 1H), 8.43 (ddd, J=8.5, 2.6, 1.4 Hz, 1H), 8.75 (dd, J=5.5, 1.4 Hz, 1H), 8.88 (d, J=2.6 Hz, 1H). Anal. Calcd for C12H18Cl2N2.0.5H2O: C, 53.34; H, 7.09; N, 10.37. Found: C, 53.28; H, 6.96; N, 10.22.

Workup

  1. customThe solvent was removed
  2. customthe remaining solid was triturated with CH2Cl2 (2×)

Sources & evidence

ORD record
ord-4a0b85df694b48eb9e5baebab0e7dade
Source dataset
uspto-grants-1998_03
Patent number
US05733912

Reaction notes

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