Hydrochloric Acid → HCID 69830753, compound

HRID 365923Notes

Reaction equation

HRID 365923 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([O:12][CH2:13][C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH3:19])[CH:9]=[N:10][CH:11]=1.[ClH:20]>C(Cl)Cl.CCOCC>[ClH:20].[ClH:20].[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([O:12][CH2:13][C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH3:19])[CH:9]=[N:10][CH:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54246973HCID 54246973, compound

Product 1

HCID 69830753HCID 69830753, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To 5-methoxyethoxy-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine from step 198a (300 mg, 1.12 mmol) in CH2Cl2 at 0° C. was added a solution of HCl in Et2O, and the solution was stirred for 2 h. Solvent was removed and the residue was recrystallized from EtOH/Et2O to afford the title compound (225 mg, 95%): mp 196-197° C.; [α]25D +25.4° (c 0.61, MeOH); 1H NMR (D2O, 300 MHz) δ 2.05-2.15 (m, 4H), 2.65 (m, 1H), 3.00 (s, 3H), 3.65 (s, 3H), 3.72 (t, 2H, J=6.0 Hz), 3.85 (t, 2H, J=6.0 Hz), 4.25 (m, 1H), 4.62-4.66 (m, 2H), 4.80 (m, 1H), 7.42 (t, 1H, J=3.0 Hz), 8.15 (br s, 2H); MS (CI/NH3) m/z 267 (M+H)+ ; Anal. Calcd for C14H22N2O3.2 HCl: C, 49.56; H, 7.13; N, 8.26. Found: C, 49.68; H, 7.05; N, 8.18.

Workup

  1. customSolvent was removed
  2. customthe residue was recrystallized from EtOH/Et2O

Sources & evidence

ORD record
ord-e630496931e749bdac8f2434ec126805
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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