Hydrochloric Acid → 7a-(6-Fluoro-5-methyl-3-pyridinyl)-hexahydro-1h-pyrrolizine hydrochloride salt

HRID 3318Notes

Reaction equation

HRID 3318 reaction equation
[F: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][C:3]=1[CH3:16].[ClH:17]>CCOCC>[ClH:17].[F: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][C:3]=1[CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 189347167a-(6-fluoro-5-methyl-3-pyridinyl)-hexahydro-1H-pyrrolizine

Product 1

HCID 189347497a-(6-Fluoro-5-methyl-3-pyridinyl)-hexahydro-1h-pyrrolizine hydrochloride saltYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

7a-(6-Fluoro-5-methyl-3-pyridinyl)-hexahydro-1H-pyrrolizine (115 mg, 0.52 mmol, from step 18d) was dissolved in Et2O, 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 (white needles, 92 mg, 69%): mp 170-171° C.; 1H NMR (D2 O, 300 MHz) δ2.12-2.47 (m, 9H), 2.56-2.66 (m, 2H), 3.32-3.41 (m, 2H), 3.77-3.86 (m, 2H), 7.94 (m, 1H), 8.14 (m, 1H); MS (CI/NH3) m/z: 221 (M+H)+ ; MS (CI/NH3): m/z 221 (M+H+). Anal. Calcd for C13H17FN2.HCl: C, 60.82; H, 7.07; N, 10.91. Found: C, 60.83; H, 6.80; N, 10.63.

Workup

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

Sources & evidence

ORD record
ord-457e5f8be8b3495ea5aaa4132c8195ea
Source dataset
uspto-grants-1998_03
Patent number
US05733912

Reaction notes

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