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

HRID 3312Notes

Reaction equation

HRID 3312 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]23[CH2:15][CH2:14][CH2:13][N:12]2[CH2:11][CH2:10][CH2:9]3)[CH:7]=1.CCOCC.[ClH:21]>C(Cl)Cl>[ClH:21].[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]23[CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15]3)[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 189347307a-(3-hydroxy-5-pyridinyl)-hexahydro-1H-pyrrolizine

Product 1

HCID 189347297a-(3-Hydroxy-5-pyridinyl)-hexahydro-1h-pyrrolizine hydrochloride saltYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7a-(3-Hydroxy-5-pyridinyl)-hexahydro-1H-pyrrolizine (150 mg, 0.56 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 dried to afford the title compound as a white powder (114 mg, 91%): mp 175°-180° C. (dec.); 1H NMR D2O, 300 MHz) δ2.11-2.63 (m, 8H), 3.35-3.44 (m, 2H), 3.80-3.89 (m, 2H), 7.66 (dd, J=2.4, 2.0 Hz, 1H), 8.23 (d, J=2.4 Hz, 1H), 8.29 (d, J=2.0 Hz, 1H); MS (CI/NH3) m/z: 205 (M+H)+. Anal. Calcd for C12H16N2O.HCl: C, 53.40; H, 6.65; N, 10.38. Found: C, 53.55; H, 6.62; N, 10.24.

Workup

  1. customThe solvent was removed
  2. customthe solid was dried

Sources & evidence

ORD record
ord-024cc166a8ad4750aa817d400f40ba7a
Source dataset
uspto-grants-1998_03
Patent number
US05733912

Reaction notes

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